Journal
ORGANIC LETTERS
Volume 10, Issue 19, Pages 4359-4362Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801792k
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Funding
- NIH [CA-70329]
- American Cancer Society-Michael Schmidt Postdoctoral Fellowship
- National Institutes of Health,
- National Cancer Institute [FCA 121716A]
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In a quest to develop an effective, scalable synthesis of (+)-spongistatin 1 (1), we devised a concise, third-generation scalable synthesis of (+)-7, the requisite F-ring tetrahydropyran aldehyde, employing a proline-catalyzed cross-aldol reaction. Subsequent elaboration to (+)-EF Wittig salt (+)-3, followed by union with advanced ABCD aldehyde (-)-4, macrolactonization and global deprotection permitted access to >1.0 g of totally synthetic (+)-spongistatin 1 (1).
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