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Synlett 2019; 30(20): 2253-2257
DOI: 10.1055/s-0039-1690267
DOI: 10.1055/s-0039-1690267
letter
Construction of the ACDE Ring System of Calyciphylline A-type Alkaloids via Intramolecular Diels–Alder Reaction of a Tetrasubstituted Olefin
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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690267.
- Supporting Information
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For reviews of the synthetic studies of Daphniphyllum alkaloids, see:
Additionally, compounds closely related to the calyciphylline A-type subfamily, including daphmanidine E, calyciphylline N, and daphenylline have been recently synthesized: