The solution to a deep stereochemical conundrum: Studies toward the tetrahydroisoquinoline alkaloids

被引:23
作者
Chan, C [1 ]
Zheng, SP [1 ]
Zhou, BS [1 ]
Guo, J [1 ]
Heid, RM [1 ]
Wright, BJD [1 ]
Danishefsky, S [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
antitumor agents; asymmetric synthesis; Mannich cyclization; natural products; total synthesis;
D O I
10.1002/anie.200503982
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Facile construction of subunits 1 and 2 allowed the rapid assembly of the pentacyclic ring system 3 of the cytotoxic tetrahydroisoquinoline alkaloids. A surprising participation reaction was discovered, which necessitated revision of the stereochemical assignments of key intermediates en route to 3. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1749 / 1754
页数:6
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[21]   Synthetic explorations in the saframycin-ecteinascidin series: construction of major chiral subunits through catalytic asymmetric induction [J].
Zhou, BS ;
Edmondson, S ;
Padron, J ;
Danishefsky, SJ .
TETRAHEDRON LETTERS, 2000, 41 (13) :2039-2042
[22]   A novel face specific Mannich closure providing access to the saframycin-ecteinascidin series of piperazine based alkaloids [J].
Zhou, BS ;
Guo, JS ;
Danishefsky, SJ .
TETRAHEDRON LETTERS, 2000, 41 (13) :2043-2046