scholarly journals Chiral synthesis of polyketide-drived natural products. 43. Stereoselective synthesis of optically active 4-ethyl-3,5-dihydroxy-2-methylpentyl derivatives. A basic building block with three contiguous chiral centers of polyether antibiotics.

1993 ◽  
Vol 41 (11) ◽  
pp. 2044-2046 ◽  
Author(s):  
Kiyoshi HORITA ◽  
Kazuhiro TANAKA ◽  
Osamu YONEMITSU
Keyword(s):  
Natural Products ◽  
Building Block ◽  
Stereoselective Synthesis ◽  
Optically Active ◽  
Basic Building Block ◽  
Chiral Synthesis ◽  
Chiral Centers

scholarly journals Use of (S)-trans-γ-Monocyclofarnesol as a Useful Chiral Building Block for the Stereoselective Synthesis of Diterpenic Natural Products

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Stefano Serra ◽  
Alessandra A. Cominetti ◽  
Veronica Lissoni
Keyword(s):  
Natural Products ◽  
Building Block ◽  
Stereoselective Synthesis ◽  
Allyl Acetate ◽  
Chiral Building Block ◽  
Sulfone Derivative ◽  
Key Steps ◽  
First Time ◽  
Unambiguous Assignment ◽  
Comprehensive Study

A comprehensive study of the exploitation of ( S)- trans-γ-monocyclofarnesol as a useful chiral building block for the stereoselective synthesis of natural diterpene derivatives is here described. The farnesol derivative (+)-1 was used as starting material in the preparation of the diterpenes ( S)-dehydroambliol-A and ( S)-trixagol, as well as for the syntheses of the dinorditerpene ( S)-dinortrixagone and of the guanidine-interrupted terpenoid ( S)-dotofide. Key steps of the presented syntheses were the cross-coupling between an allyl acetate and a Grignard reagent, the Wittig reaction, the selective preparation of a diacylguanidine derivative and the alkylation of a sulfone derivative, followed by the reductive removal of the same functional group. It is worth noting that the natural products (+)-8, (+)-12 and (+)-15 were prepared stereoselectively for the first time, thus allowing the unambiguous assignment of their absolute configuration.

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