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Stereoselective Synthesis of the C1-C29 Part of Amphidinol 3.
- Source :
-
Journal of Organic Chemistry . 1/16/2015, Vol. 80 Issue 2, p859-871. 13p. - Publication Year :
- 2015
-
Abstract
- Stereoselective synthesis of the C1-C29 part of amphidinol 3 (AM3) was achieved. The C1-C20 part was assembled from three building blocks via regioselective cross metathesis to form the C4-C5 double bond and addition of an alkenyllithium and a lithium acetylide to two Weinreb amides followed by asymmetric reduction to form the C9-C10 and C14-C15 bonds, respectively. The C21-C29 part was synthesized via successive cross metathesis and oxa-Michael addition sequence to construct the 1,3-diol system at C25 and C27 and Brown asymmetric crotylation to introduce the stereogenic centers at C23 and C24. Coupling of the C1-C20 and C21-C29 parts was achieved by Julia-Kocienski olefination and regio- and stereoselective dihydroxylation of the C20-21 double bond in the presence of the C4-C5 and C8-C9 double bonds to afford the C1-C29 part of AM3. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 80
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 101085383
- Full Text :
- https://doi.org/10.1021/jo502322m