An asymmetric synthesis of the BC ring system of 8-epitaxoids by way of intramolecular aldol and successive stereoselective methylation reactions

DOI: 10.1246/cl.1996.483

Source and publish data:

Chemistry Letters p. 483 - 484 (1996)

Update date:2022-07-29

Topics:

Authors:

Mukaiyama, Teruaki

Shiina, Isamu

Iwadare, Hayato

Saitoh, Masahiro

Nishimura, Koji

Nishimura, Toshihiro

Ohkawa, Naoto

Sakoh, Hiroki

Saitoh, Katsuyuki

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Article abstract of DOI:10.1246/cl.1996.483

Optically active 1α-allyl-1β,11β-benzylidenedioxy-2α,10β- bis(benzyloxy)-7β,9β-isopropylidenedioxy-8α,12,12-trimethyl-4- methylenebicyclo[6.4.0]dodecane (2)¹ which corresponds to BC ring system of 8-epitaxoids was prepared in high yield from ketoaldehyde 8 via intramolecular aldol cyclization and successive stereoselective methylation reactions. The ketoaldehyde 8 was synthesized from 8-membered ring compound 3 by stereoselective Michael addition using higher-order cuprate.

Full text of DOI:10.1246/cl.1996.483

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