Tetrahedron p. 3171 - 3180 (1988)
Update date:2022-08-02
Topics:
Martin, Stephen F.
Gluchowski, Charles
Campbell, Carlton L.
Chapman, Robert C.
An efficacious, asymmetric synthesis of the 2,9-dioxabicyclo<3.3.1>nonane 4 has been completed in nine chemical steps from 4,5-dimethylfuraldehyde (8).Since enantiomerically pure 4 has been previously converted in five steps by Ireland into (+)-tirandamycic acid (3) and more recently by Schlessinger into(-)-tirandamycin A(1), this achievement constitutes in a strictly formal sense the total syntheses of these substances.The key step in the synthesis of 4 features the transformation of the enantiomerically pure furfuryl diol 25 into 29 by initial selective oxidation of the furan ring and subsequent acid-catalyzed bicycloketalization.
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