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Tetrahedron. 2017 Jan 26;73(4):359-364. doi: 10.1016/j.tet.2016.12.013. Epub 2016 Dec 11.

A total synthesis of (-)-Hortonone C.

Author information

1
Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States.
2
Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States; Department of Biology, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States.
3
Department of Biology, New Mexico Institute of Mining and Technology, Socorro NM 87801, United States.

Abstract

A total synthesis of the cytotoxic terpenoid hortonone C was accomplished and its absolute stereochemistry confirmed. Intermediate (+)-4 was synthesized using either an asymmetric conjugate addition strategy, or by elaboration of the Hajos-Parrish ketone. Reduction of (+)-4 under dissolving-metal conditions and trapping the enolate intermediate served to control the cis-stereochemistry at the ring fusion and provide a silyl enol ether necessary for ring expansion. Comparison of optical rotation data confirmed that the absolute configuration of natural hortonone C is (6S,7S,10S).

KEYWORDS:

Asymmetric Conjugate Addition; Hortonones; Hydroazulene; Hydroindane; Natural Products; Total Synthesis

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