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

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.

SUBMITTER: Wang L

PROVIDER: S-EPMC6274458 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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

Wang Li L Shou Ping-Ping PP Wei Si-Ping SP Zhang Chun C Li Shuang-Xun SX Liu Ping-Xian PX Du Xi X Wang Qin Q

Molecules (Basel, Switzerland) 20160119 1

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. ...[more]

PMID: 26797597

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