scholarly journals A concise enantioselective synthesis of the guaiane sesquiterpene (−)-oxyphyllol

2013 ◽  
Vol 9 ◽  
pp. 2028-2032 ◽  
Author(s):  
Martin Zahel ◽  
Peter Metz
Keyword(s):  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Englerin A ◽  
Epoxide Opening

(−)-Oxyphyllol was prepared in only 4 steps from an epoxy enone that already served as an intermediate for the total synthesis of the anticancer guaiane (−)-englerin A. A regio- and diastereoselective Co(II)-catalyzed hydration of the olefin and a transannular epoxide opening were used as the key reactions.

Intramolecular Michael Addition of N- and O-Centred Nucleophiles to Tethered Acrylates. The Role of Double-Bond Geometry in Controlling the Diastereo- selectivity of Cyclizations Leading to 2,6-Disubstituted Tetrahydropyrans and Piperidines.

1998 ◽  
Vol 51 (1) ◽  
pp. 9 ◽  
Author(s):  
Martin G. Banwell ◽  
Brett D. Bissett ◽  
Chinh T. Bui ◽  
Ha T. T. Pham ◽  
Gregory W. Simpson
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Michael Addition ◽  
Reductive Amination ◽  
Major Product ◽  
Enantioselective Synthesis ◽  
Cyclization Reactions ◽  
Glandular Secretion

The oxyanion derived from hydroxyacrylate E-(5) undergoes smooth intramolecular Michael addition to give the trans-2,6-disubstituted tetrahydropyran (7) as the major product of reaction. In contrast, the oxyanion obtained from isomer Z-(5) cyclizes to give the cis-2,6-disubstituted tetrahydropyran (6) as the major product. Such chemistry has been extended to the enantioselective synthesis of (+)-(6) the acquisition of which constitutes a formal total synthesis of acid (+)-(2), a constituent of the glandular secretion from the civet cat (Viverra civetta). Reductive amination of keto acrylate (12) affords an intermediate amine which cyclizes, in situ, to give the cis-2,6-disubstituted piperidine (26). Analogous treatment of compound (13) delivers the isomeric trans-2,6-disubstituted piperidine (27) as the exclusive product of reaction. Transition state structures have been proposed to account for the diastereoselectivities observed in all of the cyclization reactions.

Total Synthesis of Englerin A

2010 ◽  
Vol 132 (23) ◽  
pp. 8219-8222 ◽  
Author(s):  
K. C. Nicolaou ◽  
Qiang Kang ◽  
Sin Yee Ng ◽  
David Y.-K. Chen
Keyword(s):  
Total Synthesis ◽  
Englerin A

scholarly journals Development of a Divergent Route to Erythrina Alkaloids

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 327-333 ◽  
Author(s):  
Jesper L. Kristensen ◽  
Sebastian Clementson ◽  
Mikkel Jessing ◽  
Paulo J. Vital
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
19Th Century ◽  
First Generation ◽  
Second Generation ◽  
Enantioselective Synthesis ◽  
Third Generation ◽  
Synthetic Strategy ◽  
Erythrina Alkaloids ◽  
The 19Th Century

Erythrina alkaloids were identified at the end of the 19th century and today, more than 100 members of the erythrinane family have been isolated. They are characterized by a unique tetracyclic, α-tertiary spiroamine scaffold. Herein we detail our efforts towards the development of a divergent enantioselective synthesis of (+)-dihydro-β-erythroidine (DHβE) – one of the most prominent members of this intriguing family of natural products.1 Introduction2 Synthetic Strategy2.1 First Generation2.2 Second Generation2.3 Third Generation2.3.1 Radical Endgame2.3.2 Completion of the Total Synthesis3 Conclusion

scholarly journals First Stereoselective Total Synthesis of Ciryneol C

SynOpen ◽  
2019 ◽  
Vol 03 (02) ◽  
pp. 59-66
Author(s):  
Ambati Sharada ◽  
Lakshmi Srinivasa Rao Kundeti ◽  
Kallaganti V. S. Ramakrishna ◽  
Kommu Nagaiah
Keyword(s):  
Total Synthesis ◽  
Coupling Reactions ◽  
Asymmetric Total Synthesis ◽  
Acetylene Derivative ◽  
Wittig Olefination ◽  
Epoxide Opening ◽  
Key Steps

The acetylene derivative Ciryneol C was isolated from the roots of C. japonicum. The asymmetric total synthesis of Ciryneol C was achieved in seven steps, with Horner–Wittig olefination, regioselective epoxide opening, and Cadiot–Chodkiewicz coupling reactions being the key steps.

Total Synthesis of (±)-Englerin A and Its Tuncated Analogues

2019 ◽  
Vol 2019 (5) ◽  
pp. 1027-1037 ◽  
Author(s):  
Colleen Reagan ◽  
Graham Trevitt ◽  
Kirill Tchabanenko
Keyword(s):  
Total Synthesis ◽  
Englerin A
Sign in / Sign up

Export Citation Format

Share Document