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Title: Synthesis of the Briarane northern hemisphere
Authors: Attapol Pinsa
Keywords: DRNTU::Engineering::Computer science and engineering
Issue Date: 2010
Source: Attapol Pinsa. (2010). Synthesis of the Briarane northern hemisphere. Doctoral thesis, Nanyang Technological University, Singapore.
Abstract: A large group of marine natural products isolated over the last few years is the briaranes. Over 300 have been isolated, all based on a ring system containing a six membered ring, a ten membered ring and a butenolide, or its oxidised form. Biological studies on the briaranes have revealed a range of activities. Our approach to the synthesis of the briaranes uses a modular approach that should be sufficiently flexible to allow for the synthesis of a variety of these natural products. The preparation of the six-membered ring containing with upper chain as a potential building block was achieved. The Robinson annulation reaction employing P-ketoesters under very mild conditions could not be used to prepare the desired cyclohexenone ester. However, the six-membered ring was obtained by an unusual Diels-Alder reaction of a sulfonyl diene. The Diels-Alder adduct was further manipulated by a series of reactions including oxidative desulfonylation, Eschenmoser-Claisen rearrangement, halo-lactonisation, and enolate hydroxylation using MoOPD.
Description: 207 p.
DOI: 10.32657/10356/47499
Rights: Nanyang Technological University
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

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