Total Synthesis of Scytophycin C. 1. Stereoselective Syntheses of the C(1)−C(18) Segment and the C(19)−C(31) Segment

2003 ◽  
Vol 5 (20) ◽  
pp. 3579-3582 ◽  
Author(s):  
Ryoichi Nakamura ◽  
Keiji Tanino ◽  
Masaaki Miyashita
Keyword(s):  
Total Synthesis ◽  
Scytophycin C ◽  
Stereoselective Syntheses

Stereoselective Total Synthesis of Copa and Ylango Sesquiterpenoids: Preparation of (−)-(1S,4S,5R,7R)-1,7-Dimethyl-4-isopropylbicyclo[3.2.1]octa-6,8-dione and(+)-(1R,4S,5S,7S)-1,7-Dimethyl-4-isopropylbicyclo[3.2.1]octa-6,8-dione

1975 ◽  
Vol 53 (19) ◽  
pp. 2827-2837 ◽  
Author(s):  
Edward Piers ◽  
Ronald W. Britton ◽  
M. Bert Geraghty ◽  
Robert J. Keziere ◽  
R. Dean Smillie
Keyword(s):  
Total Synthesis ◽  
Acetyl Chloride ◽  
Ester Hydrolysis ◽  
Keto Acid ◽  
Blocking Group ◽  
Claisen Condensation ◽  
Keto Ester ◽  
Enolate Anion ◽  
Stereoselective Syntheses ◽  
Potential Use

The efficient, stereoselective syntheses of two diastereomeric bicyclo[3.2.1]octadiones (23 and 24) are described and the potential use of these materials for the synthesis of the copa (1–5) and the ylango (7–11) sesquiterpenoids, respectively, is outlined. Conversion of (+)-carvomenthone (26) into the corresponding n-butylthiomethylene derivative 28, followed by alkylation of the latter with ethyl 2-iodopropionate, gave compound 29. Removal of the blocking group from the latter was accompanied by ester hydrolysis and afforded keto acid 30. An efficient intramolecular Claisen condensation of the corresponding ester 31 yielded (−)-(1S,4S,5R,7R)-1,7-dimethyl-4-isopropylbicyclo[3.2.1]octa-6,8-dione(23). Conversion of the known octalone 39 into the cross-conjugated keto aldehyde 41 was accomplished by standard reactions. Treatment of the latter with lithium dimethylcuprate, followed by trapping of the resultant enolate anion with acetyl chloride gave compound 42. Oxidative ozonolysis of this material yielded the keto acid 43. Esterification of the latter, followed by intramolecular Claisen condensation of the resulting keto ester 45, afforded (+)-(1R,4S,5S,7S)-1,7-dimethyl-4-isopropylbicyclo[3.2.1]octa-6,8-dione (24).

ChemInform Abstract: The Total Synthesis of Scytophycin C. Part 1. Stereocontrolled Synthesis of the C1-C32 Protected Seco Acid.

ChemInform ◽  
2010 ◽  
Vol 30 (3) ◽  
pp. no-no
Author(s):  
I. PATERSON ◽  
K.-S. YEUNG ◽  
C. WATSON ◽  
R. A. WARD ◽  
P. A. WALLACE
Keyword(s):  
Total Synthesis ◽  
Stereocontrolled Synthesis ◽  
Scytophycin C

The total synthesis of scytophycin C. Part 1: stereocontrolled synthesis of the C1C32 protected seco acid

Tetrahedron ◽  
1998 ◽  
Vol 54 (39) ◽  
pp. 11935-11954 ◽  
Author(s):  
Ian Paterson ◽  
Kap-Sun Yeung ◽  
Christine Watson ◽  
Richard A. Ward ◽  
Paul A. Wallace
Keyword(s):  
Total Synthesis ◽  
Stereocontrolled Synthesis ◽  
Scytophycin C
Sign in / Sign up

Export Citation Format

Share Document