The Second Total Synthesis of Diazonamide A | Zendy

Nicolaou K. C. | Zendy; Bheema Rao Paraselli | Zendy; Hao Junliang | Zendy; Reddy Mali Venkat | Zendy; Rassias Gerasimos | Zendy; Huang Xianhai | Zendy; Chen David Y.K. | Zendy; Snyder Scott A. | Zendy

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The Second Total Synthesis of Diazonamide A

Author(s) -

Nicolaou K. C.,

Bheema Rao Paraselli,

Hao Junliang,

Reddy Mali Venkat,

Rassias Gerasimos,

Huang Xianhai,

Chen David Y.K.,

Snyder Scott A.

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200351112

Subject(s) - total synthesis , oxindole , indoline , natural product , cascade , sequence (biology) , stereochemistry , closing (real estate) , chemistry , combinatorial chemistry , ring (chemistry) , organic chemistry , biochemistry , business , chromatography , catalysis , finance

The uniquely woven , highly strained molecular architecture and the potent antitumor activity of diazonamide A ( 1 ) make this natural product an attractive synthetic target. The key steps in this total synthesis of 1 include a novel SmI 2 ‐induced ring‐closing cascade sequence and an unusual oxidation of an indoline to an oxindole in the presence of Pd(OH) 2 /C.

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