Total synthesis of cruentaren B

Chakraborty, Tushar Kanti ; Chattopadhyay, Amit Kumar (2008) Total synthesis of cruentaren B Journal of Organic Chemistry, 73 (9). pp. 3578-3581. ISSN 0022-3263

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A convergent total synthesis of the cytotoxic natural product cruentaren B is completed in 26 steps (longest linear sequence) with an overall yield of 7.1%. For the construction of the C1-C11 benzolactone fragment of the molecule, the key steps used were O-methylation, using a Mitsunobu reaction, a Stille coupling method to construct the C7-C8 bond, and a Brown's asymmetric crotylboration reaction for the direct enantioselective installation of the two chiral centers present in this fragment. For diastereoselective installation of the chiral centers in the C12-C20 polyketide fragment, an Evans syn aldol reaction on a chiral aldehyde, derived from methyl (R)-3-hydroxyl-2-methylpropionate, and subsequently a Mukaiyama aldol reaction were employed. For the construction of the C21-C28 tail, a "non-Evans" syn aldol reaction was used. The three fragments were coupled by an SN2 reaction and a Wittig olefination reaction followed by standard functional group manipulations to furnish the target molecule.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:20453
Deposited On:20 Nov 2010 14:29
Last Modified:20 Nov 2010 14:29

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