Total synthesis of (±)-epithuriferic acid methyl ester via Diels–Alder reaction

2016 ◽  
Vol 14 (5) ◽  
pp. 1822-1830 ◽  
Author(s):  
Marek Koprowski ◽  
Piotr Bałczewski ◽  
Krzysztof Owsianik ◽  
Ewa Różycka-Sokołowska ◽  
Bernard Marciniak
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Acid Methyl Ester ◽  
Alder Reaction ◽  
Diels Alder ◽  
Natural Sources ◽  
Diels Alder Reaction ◽  
Acid Methyl

The first total synthesis of (±)-epithuriferic acid methyl ester from non-natural sources, in four steps (20% overall yield) is reported in this paper.

Total synthesis of the complex taxane diterpene canataxpropellane

Science ◽  
2020 ◽  
Vol 367 (6478) ◽  
pp. 676-681 ◽  
Author(s):  
Fabian Schneider ◽  
Konstantin Samarin ◽  
Simone Zanella ◽  
Tanja Gaich
Keyword(s):  
Total Synthesis ◽  
Anticancer Agent ◽  
Alder Reaction ◽  
Diels Alder ◽  
Core Structure ◽  
Natural Sources ◽  
The Core ◽  
Diels Alder Reaction ◽  
Cyclobutane Ring ◽  
Quaternary Carbons

Canataxpropellane belongs to the medicinally important taxane diterpene family. The most prominent congener, Taxol, is one of the most commonly used anticancer agent in clinics today. Canataxpropellane exhibits a taxane skeleton with three additional transannular C–C bonds, resulting in a total of six contiguous quaternary carbons, of which four are located on a cyclobutane ring. Unfortunately, isolation of canataxpropellane from natural sources is inefficient. Here, we report a total synthesis of (–)-canataxpropellane in 26 steps and 0.5% overall yield from a known intermediate corresponding to 29 steps from commercial material. The core structure of the (–)-canataxpropellane (2) was assembled in two steps using a Diels–Alder/ortho-alkene-arene photocycloaddition sequence. Enantioselectivity was introduced by designing chiral siloxanes to serve as auxiliaries in the 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.

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