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Stereocontrolled route to a key intermediate for the synthesis of maytansine

โœ Scribed by E.J. Corey; Mark G. Bock

Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
210 KB
Volume
16
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

We have undertaken a synthesis of this substance as part of a broader program in the area of biologically active macrocyclic natural products. One attractive approach to the synthesis of maytansine involves the introduction of chiraltty at carbons 3, 4, 5, 10, and 9 after formation of the macro ring, thereby allowing control of stereochemistry by cyclic conformational effects. The acyclic intermediate g, which corresponds to carbons 5 to 9 of maytansine, appeared to us to be especially valuable in such a scheme, since carbons 6 and 7 in principle direct the generation of the other stereocenbrs and also since the elaboration of tbis intermediate is possible from both ends, in either order. An efficient stereocontrolled synthesis of 2 is reported herein along with methodology for further transformations.

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