Total synthesis of 5-epi-Torrubiellutin C and its biological evaluation

Mahipal, Bodugam ; Singh, Ashita ; Ummanni, Ramesh ; Chandrasekhar, Srivari (2013) Total synthesis of 5-epi-Torrubiellutin C and its biological evaluation RSC Advances, 3 (36). p. 15917. ISSN 2046-2069

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Official URL: http://doi.org/10.1039/c3ra42127a

Related URL: http://dx.doi.org/10.1039/c3ra42127a

Abstract

The total synthesis of 5-epi-Torrubiellutin C is described in a fully stereocontrolled manner and linear sequence involving high yielding steps. The synthetic strategy involves the dicyclohexylboron chloride mediated Paterson's aldol protocol, Horner–Emmons olefination, TiCl4 mediated syn-aldol reaction and ring closing metathesis (RCM) as the key steps. Furthermore, the resultant epimer was evaluated for cytotoxicity against DU145 (prostate), MCF-7 (breast) and A549 (lung) cancer cell lines, and the results showed that the 5-epi-Torrubiellutin C is as good as the natural product in bioassays.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry
ID Code:131339
Deposited On:06 Dec 2022 10:36
Last Modified:06 Dec 2022 10:36

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