A total synthesis of the C/D rings - side chain fragment of vitamin D and sterols, using Mukaiyama - Michael conjugate addition

1993 ◽  
Vol 34 (41) ◽  
pp. 6627-6630 ◽  
Author(s):  
Stanisław Marczak ◽  
Jerzy Wicha
Keyword(s):  
Vitamin D ◽  
Total Synthesis ◽  
Conjugate Addition ◽  
Side Chain ◽  
Chain Fragment

Total synthesis of herboxidiene, a complex polyketide from Streptomyces species A7847

2000 ◽  
Vol 72 (9) ◽  
pp. 1631-1634 ◽  
Author(s):  
Martin Banwell ◽  
Malcolm McLeod ◽  
Rajaratnam Premraj ◽  
Gregory Simpson
Keyword(s):  
Acetic Acid ◽  
Total Synthesis ◽  
Acid Derivative ◽  
Side Chain ◽  
Streptomyces Species ◽  
Chain Fragment

A formal total synthesis of the polyketide herboxidiene (1) has been achieved by Horner-Wittig coupling of the side-chain fragment 12-epi-(2) with the tetrahydropyran-2-acetic acid derivative (3) followed by desilylation of the resulting triene (19) and hydroxyl-directed mono-epoxidation of the ensuing bis-homoallylic alcohol (20).

Structure-activity relationship study of vitamin D analogs with oxolane group in their side chain

2017 ◽  
Vol 134 ◽  
pp. 86-96 ◽  
Author(s):  
Anna Y. Belorusova ◽  
Andrea Martínez ◽  
Zoila Gándara ◽  
Generosa Gómez ◽  
Yagamare Fall ◽  
...  
Keyword(s):  
Vitamin D ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Side Chain ◽  
Vitamin D Analogs ◽  
Structure Activity ◽  
Relationship Study

ChemInform Abstract: Total Synthesis of a New 7-Deoxyidarubicinone Derivative Through the Functionalization of an A-Ring Side Chain.

ChemInform ◽  
2000 ◽  
Vol 31 (49) ◽  
pp. no-no
Author(s):  
Young S. Rho ◽  
Hyun Kyoung Ko ◽  
Wan-Joong Kim ◽  
Dong Jin Yoo ◽  
Heun Soo Kang
Keyword(s):  
Total Synthesis ◽  
Side Chain

Organometallics in prostaglandin synthesis

1988 ◽  
Vol 326 (1592) ◽  
pp. 579-585 ◽  
Keyword(s):  
Conjugate Addition ◽  
Prostaglandin Synthesis ◽  
Side Chain ◽  
Prostaglandin E ◽  
Controlled Synthesis ◽  
One Pot ◽  
Naturally Occurring ◽  
Chain Unit ◽  
Alkyl Iodides

An extremely short way to prostaglandins has been opened by combining the newly devised organometallic methodologies. Convergent, one-pot creation of the prostanoid framework is achieved by organocopper conjugate addition of the S-configurated ω-side-chain unit to (R)-4-trialkylsiloxy-2-cyclopentenone followed by the organotin-aided trapping of the enolate intermediate by α-side-chain alkyl iodides. Prostaglandin E 2 can be prepared in only three steps from the chiral building units. The protected 5,6-didehydro-PGE 2 derivatives thus obtained serve as common intermediates for the synthesis of a variety of naturally occurring prostaglandins including prostacyclin. This approach is also useful for the controlled synthesis of isocarbacyclin.

The Thioacetate Approach to the Synthesis of the Side Chain of Vitamin D Metabolites and Analogues.

ChemInform ◽  
2003 ◽  
Vol 34 (47) ◽  
Author(s):  
Yagamare Fall ◽  
Ousmane Diouf ◽  
Generosa Gomez ◽  
Tamara Bolano
Keyword(s):  
Vitamin D ◽  
Side Chain ◽  
Vitamin D Metabolites
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