151122-98-4Relevant articles and documents
A unified total synthesis of the immunomodulators (-)-rapamycin and (-)-27-demethoxyrapamycin: Assembly of the common C(1-20) perimeter and final elaboration
Smith III, Amos B.,Condon, Stephen M.,McCauley, John A.,Leazer Jr., Johnnie L.,Leahy, James W.,Maleczka Jr., Robert E.
, p. 962 - 973 (2007/10/03)
The potent, naturally occurring immunomodulators (-)-rapamycin (1) and (-)-27-demethoxyrapamycin (2) have been synthesized via a unified and highly convergent strategy. In the preceding paper we discussed the construction of common building blocks A-C and their linkage to provide the C(21-42) segments of 1 and 2. Herein we describe model studies of triene generation and hydroxyl deprotection, the preparation and coupling of building blocks D and E, a two-step protocol for macrocycle formation via union of the ABC and DE subtargets, and completion of the total syntheses. The synthesis of 27-demethoxyrapamycin (2) confirmed the assigned structure.
DEGRADATION OF RAPAMYCIN: RETRIEVAL OF MAJOR INTACT SUBUNITS.
Yohannes, Daniel,Danishefsky, Samuel J.
, p. 7469 - 7472 (2007/10/02)
The degradation of rapamycin has made available key substructures which have defined the structures of advanced synthetic intermediates.
