Total Synthesis of Marinomycins A-C and of Their Monomeric Counterparts Monomarinomycin A and iso-Monomarinomycin A
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- 作者：K. C. Nicolaou ; Andrea L. Nold ; Robert R. Milburn ; Corinna S. Schindler ; Kevin P. Cole ; Junichiro Yamaguchi
- 刊名：Journal of the American Chemical Society
- 出版年：2007
- 出版时间：February 14, 2007
- 年：2007
- 卷：129
- 期：6
- 页码：1760 - 1768
- 全文大小：262K
- 年卷期：v.129,no.6(February 14, 2007)
- ISSN：1520-5126
文摘
Marinomycins A-C (1-3), and their monomeric analogues monomarinomycin A (m-1) and iso-monomarinomycin A (m-2), were synthesized by a convergent strategy from key building blocksketophosphonate 5, aldehyde 6, and dienyl bromide carboxylic acid 7. The first attempt to constructmarinomycin A [1, convertible to marinomycins B (2) and C (3) by light] by direct Suzuki-type dimerization/cyclization of boronic acid dienyl bromide 4 led to premature ring closure to afford, after global desilylation,monomarinomycin A (m-1) and iso-monomarinomycin A (m-2) in good yield and only small amounts (
2%)of the desired product. A subsequent stepwise approach based on Suzuki-type couplings improvedconsiderably the overall yield of marinomycin A (1), and hence of marinomycins B (2) and C (3). Alternativedirect dimerization approaches based on the Stille and Heck coupling reactions also led to monomarinomycins A (m-1 and m-2), but failed to deliver useful amounts of marinomycin A (1).
2%)of the desired product. A subsequent stepwise approach based on Suzuki-type couplings improvedconsiderably the overall yield of marinomycin A (1), and hence of marinomycins B (2) and C (3). Alternativedirect dimerization approaches based on the Stille and Heck coupling reactions also led to monomarinomycins A (m-1 and m-2), but failed to deliver useful amounts of marinomycin A (1).