Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam

Von Oppolzer, Wolfgang; Walther, Eric Pierre Ernest; Perez Balado, Juan Carlos; De Brabander, Jef

doi:10.1016/s0040-4039(96)02408-2

Scientific article

English

Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam

ContributorsVon Oppolzer, Wolfgang; Walther, Eric Pierre Ernest; Perez Balado, Juan Carlos; De Brabander, Jef

Published inTetrahedron letters, vol. 38, no. 5, p. 809-812

Publication date1997-02-03

First online date2000-05-30

Abstract

The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from N-propionylbornanesultament-2 yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6 → 7) followed by saponification of the sultam moiety (7 → 4) provided the Prelog-Djerassi lactonic acid 4 in a three step sequence in 61–71% overall yield. The Prelog-Djerassi lactonic acid 4 was synthesised in three steps (61–71% overall yield) starting from meso dialdehyde 5 utilizing a group-selective aldolization as a key step.

Affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang et al. Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam. In: Tetrahedron letters, 1997, vol. 38, n° 5, p. 809–812. doi: 10.1016/s0040-4039(96)02408-2

Article (Published version)

Identifiers

PID : unige:155665
DOI : 10.1016/s0040-4039(96)02408-2

Commercial URLhttps://linkinghub.elsevier.com/retrieve/pii/S0040403996024082

ISSN of the journal0040-4039

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Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam

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