Studies on the Total Synthesis of Disorazole C1. An Advanced Macrocycle Intermediate

Synthesis of protected tetradehydro-(6,6‘-S)-(14,14‘-S)-(16,16‘-R)-disorazole (3), a potential precursor to the natural product disorazole C 1 (1), is described. Key features of this work include (a) an unprecedented sequential 1,5 O → O silyl rearrangement/Horner−Wadsworth−Emmons reaction used to c...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 66; no. 18; pp. 6037 - 6045
Main Authors Hillier, M. C, Price, A. T, Meyers, A. I
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 07.09.2001
Subjects
Antifungal Agents - chemical synthesis
Macrolides
Oxazoles - chemical synthesis
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Summary:Synthesis of protected tetradehydro-(6,6‘-S)-(14,14‘-S)-(16,16‘-R)-disorazole (3), a potential precursor to the natural product disorazole C 1 (1), is described. Key features of this work include (a) an unprecedented sequential 1,5 O → O silyl rearrangement/Horner−Wadsworth−Emmons reaction used to construct 18, (b) a highly convergent Sonogashira reaction between the dienyl iodide 7 and the alkyne 8 to assemble the dienyne monomeric fragment 5, and (c) the selective cyclization of 5 to give either the cyclic monomer 23 or the dimer 3.
Bibliography:istex:7D2AE6E4AF083A7C480E5316E8E0474AFC426FDD
ark:/67375/TPS-R4KGLMVH-R
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010249e