scholarly journals Synthetic studies on clerodane diterpenoids. The total synthesis of (±)-2-oxo-5α,8α-13,14,15,16-tetranorclerod-3-en-12-oic acid

1997 ◽  
Vol 75 (6) ◽  
pp. 646-655 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Kak-Shan Shia ◽  
Yongxin Han ◽  
Daqing Sun ◽  
Yu Wang
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Approach ◽  
Racemic Form ◽  
Diels Alder Reaction ◽  
Stereogenic Centers ◽  
The Face ◽  
Clerodane Diterpenoids ◽  
Synthetic Studies

A general synthetic approach to diterpenoids of the cis-clerodane family has been developed, leading to the first total synthesis, in racemic form, of 2-oxo-5α,8α-13,14,15,16-tetranorclerod-3-en-12-oic acid (2). The key operation involved is the face-selective Diels–Alder reaction of dienone ester 10 with trans-piperylene, giving rise to adduct 11 containing the decalin nucleus and correct stereogenic centers common to many cis-clerodane diterpenoids. Keywords: cis-clerodanes, general synthetic approach, total synthesis, face-selective Diels–Alder reaction.

An intermolecular Diels–Alder approach to (±)-isoacanthodoral

1994 ◽  
Vol 72 (12) ◽  
pp. 2416-2427 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Gerardo Ulibarri ◽  
Lloyd A. K. Nelson
Keyword(s):  
Total Synthesis ◽  
Boron Trifluoride ◽  
Alder Reaction ◽  
Diels Alder ◽  
Racemic Form ◽  
Diels Alder Reaction

The total synthesis of marine sesquiterpenoid isoacanthodoral (3), in racemic form, has been accomplished, using the boron trifluoride catalyzed Diels–Alder reaction of dienone ester 4 and isoprene as the key step.

Unified Approach to ent-Eudesmane-type Terpenoid Synthesis: Total Synthesis of Sinupol and Eutyscoparin A

Synthesis ◽  
2021 ◽  
Author(s):  
Koichiro Ota ◽  
Kazuo Kamaike ◽  
Hiroaki Miyaoka
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Large Class ◽  
Methyl Ketone ◽  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Approach ◽  
Unified Approach ◽  
Diels Alder Reaction

ent-Eudesmane-type terpenoids constitute a large class of natural products derived from plants, animals, and bacteria. We describe a synthetic approach to two ent-eudesmane-type terpenoids, sinupol, and eutyscoparin A, that relies on a key π-facial- and endo/exo-selective intramolecular Diels–Alder reaction to set the C-5–C-10 stereotriads. Further key transformations of trans-fused decalin include conversion to methyl ketone via a versatile thioester intermediate and appropriate functionalization toward target compounds.

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 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
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