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Molecules 2016, 21(1), 112; doi:10.3390/molecules21010112

Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes

1
Department of Medicinal Chemistry, Sichuan Medical University, Luzhou 646000, China
2
Key Laboratory of Medicinal Electrophysiology of Ministry of Education, Sichuan Medical University, Luzhou 646000, China
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 6 December 2015 / Revised: 6 January 2016 / Accepted: 7 January 2016 / Published: 19 January 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [2425 KB, uploaded 19 January 2016]   |  

Abstract

An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst with high selectivity, and the final product can be obtained in only six steps. View Full-Text
Keywords: falcarindiol analogues; total synthesis; diynol; BINOL; asymmetric addition; alkyne falcarindiol analogues; total synthesis; diynol; BINOL; asymmetric addition; alkyne
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Wang, L.; Shou, P.-P.; Wei, S.-P.; Zhang, C.; Li, S.-X.; Liu, P.-X.; Du, X.; Wang, Q. Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes. Molecules 2016, 21, 112.

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