Total synthesis of (+)-blastmycinone and formal synthesis of (+)-antimycin A3b

Chakraborty, Tushar Kanti ; Chattopadhyay, Amit Kumar ; Ghosh, Subhash (2007) Total synthesis of (+)-blastmycinone and formal synthesis of (+)-antimycin A3b Tetrahedron Letters, 48 (7). pp. 1139-1142. ISSN 0040-4039

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The formal synthesis of (+)-antimycin A3b and the total synthesis of (+)-blastmycinone were achieved using, as a key step, a method developed by us for the synthesis of 2-methyl-1,3-diols via Ti(III)-mediated diastereo- and regioselective opening of trisubstituted 2,3-epoxy alcohols, to carry out the stereoselective construction of the hydroxy-acid segment. An interesting intramolecular radical translocation took place during the epoxide opening process transforming its vicinal PMB-ether in situ, into an '1,2-O-(p-methoxy)benzylidene' ring.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Antimycin A3b; Blastmycinone; Epoxide Opening; 2-Alkyl-1; 3-diol
ID Code:20499
Deposited On:20 Nov 2010 14:25
Last Modified:20 Nov 2010 14:25

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