Synthetic Approaches to Rapamycin. 3. Synthesis of a C1-C21 Fragment

Laurence Harris; Krzysztof Jarowicki; Philip Kocienski; Richard Bell

doi:10.1055/s-1996-5604

Synlett 1996; 1996(9): 903-905
DOI: 10.1055/s-1996-5604

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Synthetic Approaches to Rapamycin. 3. Synthesis of a C1-C21 Fragment

Laurence Harris, Krzysztof Jarowicki, Philip Kocienski^* , Richard Bell

^*Department of Chemistry, The University, Southampton, SO17 1BJ, UK, FAX: 0044 1703 678825, E-Mail: pjk1@soton.ac.uk

Abstract

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Key steps in two alternative approaches to the C10-C21 fragments 4 and 17 of the immunosuppressant rapamycin employ catalytic asymmetric allylation and catalytic asymmetric hydrogenation to introduce the first stereogenic centre at C14. Appendage of C1-C9 via trapping of an a-oxoketene intermediate generates the C1-C21 fragment 5.

rapamycin - asymmetric allylation - asymmetric hydrogenation - Heck reaction - immunosuppressant - ketenedithioacetal - α-oxoketene

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