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 inOrganic letters Vol. 7; no. 7; pp. 1243 - 1245
Main Authors Quinn, Kevin J, Isaacs, André K, DeChristopher, Brian A, Szklarz, Stephanie C, Arvary, Rebecca A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.03.2005
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Furans - chemical synthesis
Lactones - chemistry
Molecular Structure
Physical Sciences
Plants, Medicinal - chemistry
Rollinia - chemistry
Science & Technology
Stereoisomerism
ANNONACEOUS ACETOGENINS
METATHESIS
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/ol047352l