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Total Synthesis of the Potent HIF-1 Inhibitory Antitumor Natural Product, (8R)-Mycothiazole, via Baldwin-Lee CsF/Cul sp3-sp2-Stille Cross-Coupling. Confirmation of the Crews Reassignment
被引：9
|作者：
Wang, Liping
Hale, Karl J.
[1
]
机构：
[1] Queens Univ Belfast, Sch Chem & Chem Engn, Belfast BT9 5AG, Antrim, North Ireland
关键词：
POLYKETIDE HETEROCYCLE;
MARINE SPONGE;
MYCOTHIAZOLE;
(-)-MYCOTHIAZOLE;
METATHESIS;
RING;
D O I：
10.1021/acs.orglett.5b01966
中图分类号：
O62 [有机化学];
学科分类号：
070303 ;
081704 ;
摘要：
A convenient asymmetric total synthesis of the potent HIF-1 inhibitory antitumor natural product, (-)- or (+)-(8R)-mycothiazole (1), is described. Not only does our synthesis confirm the 2006 structural reassignment made by Crews (Crews, P., et al. J. Nat. Prod. 2006, 69, 145), it revises the [a]p data previously reported for this molecule in MeOH from -13.7 degrees to +42.3 degrees. The newly developed route to (8R)-1 sets the C(8)-OH stereocenter via Sharpless AE/2,3-epoxy alcohol reductive ring opening and utilizes two Baldwin-Lee CsF/cat. CuI Stille cross-coupling reactions with vinylstannanes 8 and 3 to efficiently elaborate the C(1) C(4) and C(14) C(18) sectors.
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页码：4200 / 4203
页数：4
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