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Issue 34, 2017
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Total syntheses of smenothiazoles A and B

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Abstract

Concise total syntheses of smenothiazoles A (1) and B (2), two distinguished vinyl chloride containing natural products isolated from the marine sponge S. aurea, have been developed. Silastannation, Stille reaction and a carefully controlled desilylchlorination were employed as key steps to construct unique polyketide acid fragments, and the optimized reaction conditions avoided migration of 2,5-diene to a 2,4-conjugated system. This report unambiguously confirmed the structures of both natural products.

Graphical abstract: Total syntheses of smenothiazoles A and B

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Publication details

The article was received on 23 Jul 2017, accepted on 09 Aug 2017 and first published on 09 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01818E
Citation: Org. Biomol. Chem., 2017,15, 7196-7203
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    Total syntheses of smenothiazoles A and B

    X. Ma, Y. Chen, S. Chen, Z. Xu and T. Ye, Org. Biomol. Chem., 2017, 15, 7196
    DOI: 10.1039/C7OB01818E

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