Stereoselective Synthesis of (−)-(1R,1′R,5′R,7′R)-1-Hydroxy-exo-brevicomin and (+)-exo-Brevicomin from 3,4,6-Tri-O-acetyl-D-glucal

Sabitha, Gowravaram ; Maheswara Reddy, Arekuti ; Siva Sankara Reddy, Singam ; Singh Yadav, Jhillu (2013) Stereoselective Synthesis of (−)-(1R,1′R,5′R,7′R)-1-Hydroxy-exo-brevicomin and (+)-exo-Brevicomin from 3,4,6-Tri-O-acetyl-D-glucal Helvetica Chimica Acta, 96 (8). pp. 1610-1615. ISSN 0018-019X

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Official URL: http://doi.org/10.1002/Hlca.201200611

Related URL: http://dx.doi.org/10.1002/Hlca.201200611

Abstract

Stereoselective syntheses of (−)-(1R,1′R,5′R,7′R)-1-hydroxy-exo-brevicomin (1) and (+)-exo-brevicomin (2) were accomplished from 3,4,6-tri-O-acetyl-D-glucal (5; Schemes 2 and 3). Chemoselective reduction, Grignard reaction, BartonMcCombie deoxygenation, and ketalization were used as key steps.

Item Type:	Article
Source:	Copyright of this article belongs to John Wiley & Sons, Inc.
ID Code:	135753
Deposited On:	14 Aug 2023 05:03
Last Modified:	14 Aug 2023 05:03

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