Synthesis of functionalized bicyclo[3.1.0]hexanes from aucubin: An access to fused aminocyclopentitols | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

8408939

Reference Type

Journal Article

Title

Synthesis of functionalized bicyclo[3.1.0]hexanes from aucubin: An access to fused aminocyclopentitols

Author(s)

Cachet, X; Deguin, B; Tillequin, F; Rolland, Y; Koch, M

Year

2000

Is Peer Reviewed?

Yes

Journal

Helvetica Chimica Acta
ISSN: 0018-019X

Volume

Issue

Page Numbers

2812-2822

Language

English

DOI

10.1002/1522-2675(20001004)83:10<2812::AID-HLCA2812>3.0.CO;2-7

Abstract

Treatment of iodolactone 8a, having a cyclopentano[c]pyran skeleton and deriving from aucubin (1) (Scheme 1), with sodium trimethylsilanolate permitted a straightforward rearrangement to bicyclo[3.1.0]hexenes 10a and 10b (Schemes 3 and 4). Introduction of an N-atom via a modified Curtius reaction provided an easy entry to fused aminocyclopentitols (Schemes 4 and 5). Target 4 is a conformationally restricted cyclopropanefused analogue of the glycosidase inhibitors mannostatins A (2) and B (3).