ChemInform Abstract: Chiral Synthesis of Polyketide-Derived Natural Products. Part 43. Stereoselective Synthesis of Optically Active 4-Ethyl-3,5-dihydroxy-2- methylpentyl Derivatives. A Basic Building Block with Three Contiguous Chiral Centers of Polyethe

ChemInform ◽  
2010 ◽  
Vol 25 (19) ◽  
pp. no-no
Author(s):  
K. HORITA ◽  
K. TANAKA ◽  
O. 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.

Sign in / Sign up

Export Citation Format

Share Document