Synthesis of the C9–C25 Subunit of Spirastrellolide B

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• 作者：Soma Maitra ; Mahipal Bodugam ; Salim Javed ; Paul R. Hanson
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3094-3097
• 全文大小：406K
• 年卷期：0
• ISSN：1523-7052

文摘

The synthesis of the C9–C25 subunit of the marine natural product spirastrellolide B is reported. The key synthetic features included the union of the two key fragments 5 and 6 via a Suzuki–Miyaura coupling reaction and a late-stage, one-pot sequential deprotection/cascade Achmatowicz rearrangement–spiroketalization to install the key spirocyclic intermediate present in the C9–C25 fragment of spirastrellolide B. The synthesis of the C9–C16 fragment 6 was accomplished via a phosphate tether mediated ring-closing metathesis (RCM), a subsequent hydroboration–oxidation protocol, followed by other stereoselective transformations in a facile manner. The spirocyclic intermediate was further functionalized utilizing a Lindlar/NaBH₄ reduction protocol to furnish the C9–C25 subunit 3.