The Effect of Acetylene Substituents on a Pd II ‐Catalyzed Cycloisomerization. Total Synthesis of (–)‐Sterepolide and Assignment of Absolute Stereochemistry | Zendy

Trost Barry M. | Zendy; Hipskind Philip A. | Zendy; Chung John Y. L. | Zendy; Chan Chuen | Zendy

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The Effect of Acetylene Substituents on a Pd II ‐Catalyzed Cycloisomerization. Total Synthesis of (–)‐Sterepolide and Assignment of Absolute Stereochemistry

Author(s) -

Trost Barry M.,

Hipskind Philip A.,

Chung John Y. L.,

Chan Chuen

Publication year - 1989

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198915021

Subject(s) - cycloisomerization , cyclopentane , catalysis , chemistry , alkyne , acetylene , ligand (biochemistry) , stereochemistry , palladium , medicinal chemistry , ethylenediamine , absolute configuration , total synthesis , organic chemistry , receptor , biochemistry

Cyclopentane units in natural products such as (–)‐stereopolide 3 are not easy to synthesize. A novel route starts from the non‐terminal alkyne 1 . Its cycloisomerization to 2 is possible in the presence of palladium( II ) acetate and the ligand N,N ′‐bis(benzylidene)ethylenediamine. This catalytic system also cyclizes other enynes of the type 1 with e.g. CH 2 OCH 3 or CH 3 instead of OSiMe 2 t Bu—where Pd(OAc) 2 alone fails (R = p ‐H 3 COC 6 H 4 CH 2 ).

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