期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 49, 页码 19844-19856出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja207385y
关键词
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资金
- National Institutes of Health [GM52964]
- Welch Foundation [A-1280]
The first total synthesis of the marine toxin ()gymnodimine (1) has been accomplished in a convergent manner. A highly diastereo- and enantioselective exo-Diels Alder reaction catalyzed by a bis-oxazoline Cu(II) catalyst enabled rapid assembly of the spirocyclic core of gymnodimine. The preparation of the tetrahydrofuran fragment utilized a chiral auxiliary based anti-aldol reaction. Two major fragments, spirolactam 56 and tetrahydrofuran 55, were then coupled through an efficient Nozaki-Hiyama-Kishi reaction. An unconventional, ambient temperature t-BuLi-initiated intramolecular Barbier reaction of alkyl iodide 64 was employed to form the macrocycle. A late stage vinylogous Mukaiyama aldol addition of a silyloxyfuran to a complex cyclohexanone 83 appended the butenolide, and a few additional steps provided (-)-gymno-dimine (1). A diastereomer of the natural product was also synthesized, C4-epigymnodimine (90), derived from the vinylogous Mukaiyama aldol addition.
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