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7,7-Dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivalent of ketodicyclopentadiene: a new route to (−)-physostigmine, (−)-physovenine, and (−)-aphanorphine

✍ Scribed by Keigo Tanaka; Takahiko Taniguchi; Kunio Ogasawara

Book ID: 104211665
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 74 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)02171-7

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✦ Synopsis

A new diastereocontrolled route to three alkaloids having a quaternary benzylic stereogenic center, (-)-physostigmine, (-)-physovenine, and (-)-aphanorphine, has been developed using enantiopure 7,7-dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivalent of chiral cyclopentadienone.

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