SYNTHESIS OF A C-14',C-15' DIHYDRO DERIVATIVE OF THE SOUTH HEXACYCLIC STEROID UNIT OF CEPHALOSTATIN-1 .1. REGIOSPECIFIC RH[II]-MEDIATED INTERMOLECULAR OXYGEN ALKYLATION OF A PRIMARY NEOPENTYL ALCOHOL

被引:20
作者
BHANDARU, S [1 ]
FUCHS, PL [1 ]
机构
[1] PURDUE UNIV, DEPT CHEM, W LAFAYETTE, IN 47907 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(95)01804-Q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hecogenin acetate 5 was converted to an intermediate suitable for the construction of a C-14',C-15' dihydro derivative of the ''South'' hexacyclic spiroketal of cephalostatin 11. The key transformations include: (i) proximal functionalization of the C-18 methyl group in 17 via hypoiodite homolysis; (ii) Rhodium [II] catalyzed intermolecular oxygen alkylation of primary neopentyl hydroxyl group in 20 and (iii) intramolecular Wadsworth-Emmons reaction to provide 23, the ester precursor of aldehyde 4.
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页码:8347 / 8350
页数:4
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