Total synthesis of (+)-haplophytine

Angewandte Chemie - International Edition

Volumn 48, Issue 41, 2009, Pages 7616-7620

  Nicolaou, K C ^a,b,c   Dalby, Stephen M ^a   Li, Shuoliang ^a   Suzuki, Takahiro ^a   Chen, David Y K ^a  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Amlnal rearrangement; Natural product; Radical cyclization; Suzuki Miyaura coupling; Total synthesis

Indexed keywords

AMLNAL REARRANGEMENT; NATURAL PRODUCT; RADICAL CYCLIZATION; SUZUKI-MIYAURA COUPLING; TOTAL SYNTHESIS;

IODINE;

CYCLIZATION;

INDOLE ALKALOID; PHYTIC ACID CALCIUM MAGNESIUM SALT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PLANT; SYNTHESIS;

INDOLE ALKALOIDS; MOLECULAR STRUCTURE; PLANTS;

EID: 70349978073     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904588     Document Type: Article

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29. 2/hexanes, see ORTEP drawing below). CCDC 706349 contains the supplementary crystallographic data for 8 a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc. cam.ac.uk/data-request/cif.
30. The structural identity of 16 was confirmed by its conversion to a compound prepared independently from the related benzyl ether 16a (m.p. = 144-145 °C, EtOAc/hexanes), the major isomer obtained from an analogous oxidative coupling reaction, which proved sufficiently crystalline for X-ray crystallographic analysis (see ORTEP drawing below). See the supporting information for further details. CCDC 730565 contains the supplementary crystallographic data for 16a.
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33. We thank Professor E. J. Corey (Harvard University) for kindly providing us with an authentic sample of natural haplophytine.