Total Synthesis of (−)‐Laulimalide: Pd‐Catalyzed Stereospecific Ring Construction of the Substituted 3,6‐Dihydro[2 H ]pyran Units | Zendy

Uenishi Jun'ichi | Zendy; Ohmi Masashi | Zendy

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Total Synthesis of (−)‐Laulimalide: Pd‐Catalyzed Stereospecific Ring Construction of the Substituted 3,6‐Dihydro[2 H ]pyran Units

Author(s) -

Uenishi Jun'ichi,

Ohmi Masashi

Publication year - 2005

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.200500029

Subject(s) - pyran , stereospecificity , allylic rearrangement , ring (chemistry) , sn2 reaction , stereochemistry , chemistry , chirality (physics) , catalysis , combinatorial chemistry , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark

The potent anticancer agent (−)‐laulimalide ( 1 ) was prepared through a versatile method that should allow access to other marine natural products. Key steps included a Pd‐catalyzed 1,3 chirality transfer of an allylic alcohol. The syn ‐S N 2′‐like processes occur stereospecifically in either 6‐ endo ‐trig or 6‐ exo ‐trig fashion to give the desired 3,6‐dihydro[2 H ]pyran rings (see scheme).

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