Synlett 2019; 30(20): 2253-2257
DOI: 10.1055/s-0039-1690267
letter
© Georg Thieme Verlag Stuttgart · New York

Construction of the ACDE Ring System of Calyciphylline A-type Alkaloids via Intramolecular Diels–Alder Reaction of a Tetrasubstituted Olefin

Hugh Nakamura
,
Manami Kawakami
,
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan   Email: tsukano@pharm.kyoto-u.ac.jp   Email: takemoto@pharm.kyoto-u.ac.jp
,
Yoshiji Takemoto
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan   Email: tsukano@pharm.kyoto-u.ac.jp   Email: takemoto@pharm.kyoto-u.ac.jp
› Author Affiliations
This work was supported by a Grant-in-Aid for Scientific Research (S) (JSPS KAKENHI no. 16H06384, Y.T.), a Grant-in-Aid for JSPS fellows (H.N.) and the JSPS KAKENHI (Grant No. JP17H05051, C.T.), and JSPS KAKENHI (Grant No. JP18H04407, C.T.) in the Middle Molecular Strategy.
Further Information

Publication History

Received: 18 September 2019

Accepted after revision: 29 October 2019

Publication Date:
07 November 2019 (online)

Abstract

A concise synthesis of the ACDE tetracyclic ring system of calyciphylline A-type alkaloids was investigated. The intramolecular Diels–Alder reaction of a tetrasubstituted olefin with furan enabled the construction of the ACD ring system bearing two contiguous quaternary carbons in one step, and subsequent intramolecular [3+2] cycloaddition successfully gave the E ring.

Supporting Information

 
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