Towards the Synthesis of Lyngbyaloside B: Stereoselective Synthesis of the C1-C16 Macrolactone Core Segment

Yadav, Jhillu S. ; Haldar, Animesh ; Maity, Tapas (2013) Towards the Synthesis of Lyngbyaloside B: Stereoselective Synthesis of the C1-C16 Macrolactone Core Segment European Journal of Organic Chemistry, 2013 (15). pp. 3076-3085. ISSN 1434-193X

Full text not available from this repository.

Official URL: http://doi.org/10.1002/Ejoc.201300083

Related URL: http://dx.doi.org/10.1002/Ejoc.201300083

Abstract

A highly stereoselective synthesis of the C1–C16 macrolactone core segment of the cytotoxic macrolide lyngbyaloside B has been achieved. The synthetic strategy involved aldol additions of chlorotitanium enolates of N-propionyl thiazolidinethiones to achieve non-Evans as well as Evans syn-propionate aldol reactions as the key steps to establish four of the seven stereogenic centres present in the macrolactone core (2). The C7 hydroxy group and tertiary hydroxy group at C13 were introduced by using different strategies for the regioselective opening of epoxides generated by Katsuki–Sharpless asymmetric epoxidation. A crucial intermolecular acyl ketene trapping by the tertiary alcohol at C13, and a subsequent ring-closing metethesis reaction served to unite the northern and southern hemisphere subunits to construct the macrolactone core (2).

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc.
ID Code:135759
Deposited On:14 Aug 2023 09:14
Last Modified:14 Aug 2023 09:14

Repository Staff Only: item control page