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Chemistry of the Ginkgolides, VIII – Synthesis and Crystal Structure of a Dimeric 14,15,16-Trinorginkgolide Derivative

✍ Scribed by Weinges, Klaus ;Schick, Hartmut ;Irngartinger, Hermann ;Oeser, Thomas

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 273 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970744

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✦ Synopsis

Abstract

Treatment of the enol acetate 3‐acetoxy‐10‐methoxy‐methoxy‐2,3‐didehydro‐14,15,16‐trinorginkgolide^[2^] (2) with potassium osmate/N‐methylmorpholine N‐oxide in acetone/acetic acid solution did not yield the expected 2‐hydroxy‐3‐oxo derivative 3, but the dimeric ginkgolide (2__S__,2′S,3__R__,3′R)‐bis(10‐methoxymethoxy‐14,15,16‐trinorginkgolido)[2,3‐c;2′,3′‐e]‐1″,4″‐dioxan‐3,3′‐diol (4a). By acid hydrolysis, 4a was converted to the MOM‐deprotected dimeric product 4b. The structure of 4a was elucidated by crystal structure analysis.

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