Chakraborty, Tushar K. ; Jayaprakash, Sarva ; Laxman, Pasunoori (2001) Total synthesis of (+)-crocacin C Tetrahedron, 57 (46). pp. 9461-9467. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)00940-1
Abstract
The total synthesis of potent antifungal and cytotoxic agent (+)-crocacin C in optically pure form following a convergent strategy is described here in detail. The synthesis also established the absolute stereochemistry of the molecule having a (6S,7S,8R,9S) configuration. While C8 and C9 stereocenters were built following a Ti(IV)-mediated diastereoselective 'non-Evans' aldol reaction based on 2-oxazolidinethione chiral auxiliary, lithium dimethylcuprate opening of a C6-C7 chiral epoxide prepared by Sharpless epoxidation method established the remaining two stereocentres.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Antifungals; Cytotoxins; Aldol Reactions; Katsuki-sharpless Reactions |
| ID Code: | 20582 |
| Deposited On: | 20 Nov 2010 14:16 |
| Last Modified: | 22 May 2011 15:47 |
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