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UBC Theses and Dissertations

Studies toward the total synthesis of salicylihalamide A Chandler, Melanie K.


This thesis describes studies toward the synthesis of enamide macrolide salicylihalamide A (1). The convergent synthetic plan requires assembly of three main subunits whose eventual coupling should provide salicylihalamide A. Construction of two key fragments encompassing the sensitive (Z, Z)-diene sidechain (177) and the functionalized aromatic portion (142) of the target 1 have been realized, Compound 142 was efficiently synthesized using the accelerative effects of CuCI on the Pd(0)-catalyzed Stille coupling between o-substituted aromatic triflate 140 and allyl tributylstannane. The diene 177 was generated using a copper(l) thiophenecarboxylate mediated cross-coupling between vinyl stannane 181 and iodide 180. The reaction was stereospecific, rapid and mild enough to allow efficient construction of this hindered and labile sidechain. Preliminary investigations into the enantioselective synthesis of the remaining subunit culminated in the formation of aldehyde 95. During the course of this work a new protocol for generating Z-vinyl stannanes such as 181 from (trimethylsilyl)acetylene was also developed.

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