Asymmetric Total Synthesis of Rollicosin
The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal γ-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incor...
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| Published in | Organic letters Vol. 7; no. 7; pp. 1243 - 1245 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
31.03.2005
Amer Chemical Soc |
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| Abstract | The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal γ-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation. |
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| AbstractList | The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal γ-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation. The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation. [structure: see text] The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation. |
| Author | Szklarz, Stephanie C Isaacs, André K DeChristopher, Brian A Arvary, Rebecca A Quinn, Kevin J |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/15787477$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_tetlet_2008_09_077 crossref_primary_10_1016_j_tet_2008_10_059 crossref_primary_10_1016_j_tetlet_2009_09_179 crossref_primary_10_1016_j_tetlet_2006_10_141 crossref_primary_10_1021_jo9018649 crossref_primary_10_1002_adsc_200505361 crossref_primary_10_1021_acssuschemeng_6b01900 crossref_primary_10_1002_chem_200801439 crossref_primary_10_1002_chem_200700832 crossref_primary_10_1016_j_tet_2012_09_027 crossref_primary_10_1016_j_tetlet_2006_12_092 crossref_primary_10_1016_j_tetlet_2019_05_064 crossref_primary_10_1021_jo1002642 crossref_primary_10_1016_j_ccr_2007_03_011 crossref_primary_10_1039_C7SC04286H crossref_primary_10_1002_ejoc_200500850 crossref_primary_10_1002_ange_200903379 crossref_primary_10_3762_bjoc_9_289 crossref_primary_10_1002_chin_200534268 crossref_primary_10_1016_j_tet_2008_09_012 crossref_primary_10_1002_adsc_200600473 crossref_primary_10_1021_jo3004106 crossref_primary_10_1016_j_tetlet_2007_09_063 crossref_primary_10_1002_ejoc_200600946 crossref_primary_10_1021_ol052332k crossref_primary_10_1039_b604359c crossref_primary_10_5059_yukigoseikyokaishi_69_159 crossref_primary_10_1021_jo061190k crossref_primary_10_1021_ja0578348 crossref_primary_10_1016_j_bmc_2005_12_015 crossref_primary_10_1002_anie_200903379 crossref_primary_10_1002_ejoc_201900551 crossref_primary_10_1002_asia_202000955 crossref_primary_10_3762_bjoc_4_48 crossref_primary_10_1002_ejoc_201000187 crossref_primary_10_1016_j_bmc_2005_05_050 crossref_primary_10_1016_j_tet_2007_03_151 crossref_primary_10_1002_cctc_200900282 crossref_primary_10_1002_ejoc_200700930 |
| Cites_doi | 10.1002/anie.200200556 10.1055/s-2004.831329 10.1021/np020236b 10.1016/j.tetlet.2003.09.056 10.1021/ol049079t 10.1021/jo034470y 10.1021/ol040047f 10.1021/ja046043n 10.1021/jo026433x 10.1016/j.tetlet.2003.08.088 10.1021/jo00044a039 10.1021/ar00057a001 10.1021/cr0200872 10.1021/ja961454s 10.1016/S0008-6215(97)00151-1 10.1021/ol990909q |
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| References | CrombezRobert, C (WOS:A1997YC52000015) 1997; 303 Quinn, KJ (WOS:000224973100002) 2004; 6 Cav, A (MEDLINE:9088159) 1997; 70 Falomir, E (WOS:000184060600028) 2003; 68 Liaw, CC (WOS:000181375700023) 2003; 66 Lee, JL (WOS:000185813200030) 2003; 44 Maifeld, SV (WOS:000224219900018) 2004; 126 Virolleaud, MA (WOS:000224374600004) 2004 Alali, FQ (WOS:000079500600026) 1999; 62 WHITE, JD (WOS:A1992JL29200039) 1992; 57 Xie, HH (WOS:000183874100012) 2003; 14 Virolleaud, MA (WOS:000185941000009) 2003; 44 Mori, Y (WOS:A1996VE26600040) 1996; 118 BouzBouz, S (WOS:000224112000010) 2004; 6 SHARPLESS, KB (WOS:A1992HT85300003) 1992; 57 Burke, SD (WOS:000083701300019) 1999; 1 Scholl, M (WOS:000085171700034) 1999; 1 Marshall, JA (WOS:000181329900016) 2003; 68 Maezaki, N (WOS:000180592000003) 2003; 9 FIGADERE, B (WOS:A1995RV39400001) 1995; 28 SCHAUS SE (WOS:000227921200012.17) 1941; 63 Connon, SJ (WOS:000182901700003) 2003; 42 Deiters, A (WOS:000221418500003) 2004; 104 For CM (ol047352lb00010/ol047352lb00010_1) 2000; 42 For RCM (ol047352lb00015/ol047352lb00015_1) 2004; 126 BouzBouz S. (ol047352lb00016/ol047352lb00016_1) 2004; 6 Sharpless K. B. (ol047352lb00008/ol047352lb00008_1) 1992; 57 Crombez-Robert C. (ol047352lb00011/ol047352lb00011_2) 1997; 303 Virolleaud M. A. (ol047352lb00013/ol047352lb00013_1) 2003; 44 Burke S. D. (ol047352lb00011/ol047352lb00011_1) 1999; 1 Scholl M. (ol047352lb00012/ol047352lb00012_1) 1999; 1 For (ol047352lb00019/ol047352lb00019_1) 1941; 63 Figadére B. (ol047352lb00002/ol047352lb00002_1) 1995; 28 Mori Y. (ol047352lb00018/ol047352lb00018_1) 1996; 118 Quinn K. J. (ol047352lb00006/ol047352lb00006_1) 2004; 6 For (ol047352lb00009/ol047352lb00009_1) 2004; 104 For (ol047352lb00001/ol047352lb00001_1) 1999; 70 Lee J. L. (ol047352lb00005/ol047352lb00005_1) 2003; 44 White J. D. (ol047352lb00007/ol047352lb00007_1) 1992; 57 Liaw C. C. (ol047352lb00003/ol047352lb00003_1) 2003; 66 Xie H. H. (ol047352lb00004/ol047352lb00004_1) 2003; 14 Virolleaud M. A. (ol047352lb00013/ol047352lb00013_2) 2004 Numerous (ol047352lb00017/ol047352lb00017_1) 2003; 68 |
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| Snippet | The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal γ-lactones, is reported. The approach... The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The... [structure: see text] The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones,... |
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| SubjectTerms | Chemistry Chemistry, Organic Combinatorial Chemistry Techniques Furans - chemical synthesis Lactones - chemistry Molecular Structure Physical Sciences Plants, Medicinal - chemistry Rollinia - chemistry Science & Technology Stereoisomerism |
| Title | Asymmetric Total Synthesis of Rollicosin |
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