Stereocontrolled Construction of ABCD Tetracyclic Ring System with Vicinal All-Carbon Quaternary Stereogenic Centers of Calyciphylline A Type Alkaloids

DOI: 10.1021/acs.orglett.8b01087

Source and publish data:

Organic Letters p. 3053 - 3056 (2018)

Update date:2022-08-04

Topics:

Authors:

Sasano, Yusuke

Koyama, Junpei

Yoshikawa, Kaori

Kanoh, Naoki

Kwon, Eunsang

Iwabuchi, Yoshiharu

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Article abstract of DOI:10.1021/acs.orglett.8b01087

A unique approach to the synthesis of an ABCD tetracyclic core bearing the vicinal all-carbon quaternary stereogenic centers of the calyciphylline A type alkaloids is reported. The synthesis features two C-C bond formations at a sterically congested position: one is an intramolecular pinacol coupling to construct the central A ring; the other is a semipinacol rearrangement to construct a quaternary stereogenic center adjacent to another quaternary center.

Full text of DOI:10.1021/acs.orglett.8b01087

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