Synthesis of a New (1R)-(−)-Myrtenal-Derived Dioxadithiadodecacycle and Its Use as an Efficient Chiral Auxiliary

The new macrocycle 9 (>70% yield from hydroxythiol 10) was treated with several nucleophilic reagents (RMgX, RLi, and LiAlH4) affording carbinols 12a−j (80−96% yield, >99:1 dr). Oxidative hydrolysis of 12a,c,e, followed by LiAlH4 reduction of the resulting mixture, gave 16a,c,e in >95% ee,1...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2007-01, Vol.9 (1), p.13-16
Main Authors: Vargas-Díaz, M. Elena, Joseph-Nathan, Pedro, Tamariz, Joaquín, Zepeda, L. Gerardo
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The new macrocycle 9 (>70% yield from hydroxythiol 10) was treated with several nucleophilic reagents (RMgX, RLi, and LiAlH4) affording carbinols 12a−j (80−96% yield, >99:1 dr). Oxidative hydrolysis of 12a,c,e, followed by LiAlH4 reduction of the resulting mixture, gave 16a,c,e in >95% ee,16c being a key precursor for the preparation of fungicide 17. The absolute configuration of 9 and 12j (Nu = H) was established by single-crystal X-ray diffraction analyses and chemical correlation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062319f