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Studies Directed Towards the Synthesis of Bryostatin
Abstract
Thesis is structured in two different parts. The first part deals with the convergent and stereo selective synthesis of the C1-C10 fragment 3 of cytostatic macrolide bryostatin. Two of the three chiral centers were established via Sharpless Kinetic resolution on racemic allylic alcohol 10 followed by reduction with Red-Al. Diastereoselective transformation of the aldehyde 18 moiety to β-hydroxy ester 20 via an Aldol reaction, which is transformed to pyran ring 3 via chemical transformations are the key steps. The second part discuss the stereo-controlled asymmetric synthesis of C7-C16 fragment 4  of bryostatin. The key steps involved in this synthesis are the Jacobsen’s hydrolytic kinetic resolution and Reformatsky reaction to build the C11-C16 fragment. The vinyl Grignard has been used to construct the C7-C10 fragment. Cross-metathesis was successfully used to couple both the fragments, C7-C10 and C11-C16 to produce a key component 46. Oxa-Michael reaction has been employedto construct the pyran ring system 4.
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References and notes
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