STEREOSELECTIVE SYNTHESIS OF A CHIRAL SYNTHON, 2,2,5-TRISUBSTITUTED TETRAHYDROPYRAN, BASED ON SIMULTANEOUS 1,3-ASYMMETRIC AND 1,6-ASYMMETRIC INDUCTION VIA NUCLEOPHILIC ACETAL CLEAVAGE REACTION OF THE BICYCLIC ACETAL - A TOTAL SYNTHESIS OF (-)-MALYNGOLIDE

Authors
MAEZAKI N MATSUMORI Y SHOGAKI T SOEJIMA M TANAKA T OHISHI H IWATA C
Citation
N. Maezaki et al., STEREOSELECTIVE SYNTHESIS OF A CHIRAL SYNTHON, 2,2,5-TRISUBSTITUTED TETRAHYDROPYRAN, BASED ON SIMULTANEOUS 1,3-ASYMMETRIC AND 1,6-ASYMMETRIC INDUCTION VIA NUCLEOPHILIC ACETAL CLEAVAGE REACTION OF THE BICYCLIC ACETAL - A TOTAL SYNTHESIS OF (-)-MALYNGOLIDE, Chemical communications, (18), 1997, pp. 1755-1756
Citations number
32
Categorie Soggetti
Chemistry
Journal title
Chemical communications → ACNP
ISSN journal
13597345
Issue
18
Year of publication
1997
Pages
1755 - 1756
Database
ISI
SICI code
1359-7345(1997):18<1755:SSOACS>2.0.ZU;2-C
Abstract
A chiral 2,2,5-trisubstituted tetrahydropyran is synthesised efficient ly via facial and group selective nucleophilic acetal cleavage reactio n of a bicyclic acetal, wherein simultaneous 1,3- and 1,6-asymmetric i nduction from a sulfinyl chirality is accomplished with high diastereo selectivity; this chiral synthon is successfully applied to a total sy nthesis of(-)-malyngolide.