Total synthesis of amphilectane-type diterpenoids: (±)-8,15-diisocyano-11(20)-amphilectene

1993 ◽  
Vol 71 (9) ◽  
pp. 1484-1494 ◽  
Author(s):  
Edward Piers ◽  
Montse Llinas-Brunet ◽  
Renata M. Oballa
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Allylic Oxidation ◽  
Keto Ester ◽  
Efficient Transformation ◽  
Diels Alder Reaction ◽  
Product Mixture

A total synthesis of the structurally novel, antimicrobial diterpenoid (±)-8,15-diisocyano-11(20)-amphilectene (2) is described. Alkylation of 2-methoxycarbonyl-3-methylcyclohexanone (13) with (E)-1-(tert-butyldimethylsiloxy)-6-iodo-3-(trimethylstannyl)-2-hexene (14) provided, stereoselectively, the functionalized keto ester 15, which was converted efficiently into the diene 17. Diels–Alder reaction of 17 with acrolein, followed by base-catalyzed equilibration of the resultant product mixture, gave the aldehydes 19 (58%) and 20 (29%). Allylic oxidation of the alkene 24 (derived from 19) afforded the enone 25. Reduction (Na, NH3, t-BuOH) of 25 gave 28, which was converted, via a sequence of eight synthetic steps, into the diacid 45. Efficient transformation of the carboxyl functions of 45 into isonitrile groups completed the synthesis of (±)-2.

Total synthesis of androstanes

1979 ◽  
Vol 57 (24) ◽  
pp. 3356-3358 ◽  
Author(s):  
Masatoshi Kakushima ◽  
Jagabandhu Das ◽  
Gary R. Reid ◽  
Peter S. White ◽  
Zdenek Valenta
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Keto Ester ◽  
Diels Alder Reaction ◽  
Androstane Derivatives

A total synthesis of androstane derivatives is described. The desired configuration at C8 and at C13 is achieved in a ring C forming SnCl4-catalyzed Diels–Alder reaction. The preparation of methyl Z-2-methyl-4-oxo-2-pentenoate and the cyclization of a keto ester to a steroid 15,17-dione are also reported.

Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 2 [1]: Macrocyclization and Diels-Alder reaction

1999 ◽  
Vol 40 (14) ◽  
pp. 2769-2772 ◽  
Author(s):  
András Toró ◽  
Yuan Wang ◽  
Marc Drouin ◽  
Pierre Deslongchamps
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Model Studies ◽  
Diels Alder Reaction

ChemInform Abstract: A Total Synthesis of Actinobolin via the Intermolecular Diels-Alder Reaction of a Threonine Derived Diene.

ChemInform ◽  
1987 ◽  
Vol 18 (9) ◽  
Author(s):  
A. P. KOZIKOWSKI ◽  
T. KONOIKE ◽  
T. R. NIEDUZAK
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Catalytic Asymmetric Total Synthesis of (+)- and (−)-Paeoveitol via a Hetero-Diels–Alder Reaction

2017 ◽  
Vol 19 (3) ◽  
pp. 429-431 ◽  
Author(s):  
Tian-Ze Li ◽  
Chang-An Geng ◽  
Xiu-Juan Yin ◽  
Tong-Hua Yang ◽  
Xing-Long Chen ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Catalytic Asymmetric

Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction

1980 ◽  
Vol 102 (22) ◽  
pp. 6893-6894 ◽  
Author(s):  
William G. Dauben ◽  
Carl R. Kessel ◽  
Kazuo H. Takemura
Keyword(s):  
High Pressure ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Total synthesis of (±)-5β,8α- androst-9(11)-ene-3,17-dione

1979 ◽  
Vol 57 (24) ◽  
pp. 3354-3356 ◽  
Author(s):  
Masatoshi Kakushima ◽  
Leonard Allain ◽  
Robert A. Dickinson ◽  
Peter S. White ◽  
Zdenek Valenta
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Allylic Alcohol ◽  
Diels Alder Reaction

A total synthesis of (±)-5β,8α- androst-9(11)-ene-3,17-dione is described. The key step is a ring C forming SnCl4-catalyzed Diels–Alder reaction in which the geometry of the diene controls syn–anti stereochemistry while the catalyst guides the addition to the desired endo orientation. A preparation of ethyl E-2-methyl-4-oxo-2-butenoate and the dehydration of a tertiary allylic alcohol by the pyrolysis of the corresponding tosyl carbamate are also described.

Total synthesis of halogenated monoterpene marine natural products via the Diels-Alder reaction

1985 ◽  
Vol 50 (20) ◽  
pp. 3738-3749 ◽  
Author(s):  
Paul G. Williard ◽  
Stephen E. De Laszlo
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels–Alder reaction of C-glycosyl juglone

1996 ◽  
pp. 225-226 ◽  
Author(s):  
Goh Matsuo ◽  
Yuko Miki ◽  
Masaya Nakata ◽  
Shuichi Matsumura ◽  
Kazunobu Toshima
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

AnN,N′-Dioxide/In(OTf)3 Catalyst for the Asymmetric Hetero-Diels–Alder Reaction Between Danishefsky's Dienes and Aldehydes: Application in the Total Synthesis of Triketide

2008 ◽  
Vol 120 (7) ◽  
pp. 1328-1331 ◽  
Author(s):  
Zhipeng Yu ◽  
Xiaohua Liu ◽  
Zhenhua Dong ◽  
Mingsheng Xie ◽  
Xiaoming Feng
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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