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Literature DB >> 34766779

Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.

In-Soo Myeong¹, Nadide Hazal Avci¹, Mohammad Movassaghi¹.

Abstract

We report the first total synthesis of (-)-kopsifoline A and (+)-kopsifoline E. Our synthetic strategy features a biogenetically inspired regioselective C17-functionalization of a versatile intermediate containing the pentacyclic core of aspidosperma alkaloids. The vinylogous urethane substructure of this intermediate affords (-)-kopsifoline D via C3-C21 bond formation under the Mitsunobu reaction conditions, while it enables selective C17-functionalization en route to (-)-kopsifoline A and (+)-kopsifoline E.

Entities: Chemical

Mesh：
Aspidosperma

Year: 2021 PMID： 34766779 PMCID： PMC9048213 DOI： 10.1021/acs.orglett.1c03448

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.072

55 in total

1. Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.

Authors: Sunkyu Han; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal: J Org Chem Date: 2013-10-31 Impact factor: 4.354

2. A Desymmetrization-Based Total Synthesis of Reserpine.

Authors: Jisook Park; David Y-K Chen
Journal: Angew Chem Int Ed Engl Date: 2018-11-08 Impact factor: 15.336

3. Remarkably Efficient Iridium Catalysts for Directed C(sp²)-H and C(sp³)-H Borylation of Diverse Classes of Substrates.

Authors: Md Emdadul Hoque; Mirja Md Mahamudul Hassan; Buddhadeb Chattopadhyay
Journal: J Am Chem Soc Date: 2021-03-30 Impact factor: 15.419

4. Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors: Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal: Science Date: 2001-11-22 Impact factor: 47.728

5. Concise total synthesis and stereochemical revision of all (-)-trigonoliimines.

Authors: Sunkyu Han; Mohammad Movassaghi
Journal: J Am Chem Soc Date: 2011-06-20 Impact factor: 15.419

6. Iridium-catalyzed C-H borylation of pyridines.

Authors: Scott A Sadler; Hazmi Tajuddin; Ibraheem A I Mkhalid; Andrei S Batsanov; David Albesa-Jove; Man Sing Cheung; Aoife C Maxwell; Lena Shukla; Bryan Roberts; David C Blakemore; Zhenyang Lin; Todd B Marder; Patrick G Steel
Journal: Org Biomol Chem Date: 2014-10-07 Impact factor: 3.876

7. Pd-catalyzed C-H oxygenation with TFA/TFAA: expedient access to oxygen-containing heterocycles and late-stage drug modification.

Authors: Gang Shan; Xinglin Yang; Linlin Ma; Yu Rao
Journal: Angew Chem Int Ed Engl Date: 2012-11-19 Impact factor: 15.336

8. A concise and versatile double-cyclization strategy for the highly stereoselective synthesis and arylative dimerization of Aspidosperma alkaloids.

Authors: Jonathan William Medley; Mohammad Movassaghi
Journal: Angew Chem Int Ed Engl Date: 2012-03-12 Impact factor: 15.336

Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.

1. Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.

2. A Desymmetrization-Based Total Synthesis of Reserpine.

3. Remarkably Efficient Iridium Catalysts for Directed C(sp²)-H and C(sp³)-H Borylation of Diverse Classes of Substrates.

4. Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

5. Concise total synthesis and stereochemical revision of all (-)-trigonoliimines.

6. Iridium-catalyzed C-H borylation of pyridines.

7. Pd-catalyzed C-H oxygenation with TFA/TFAA: expedient access to oxygen-containing heterocycles and late-stage drug modification.

8. A concise and versatile double-cyclization strategy for the highly stereoselective synthesis and arylative dimerization of Aspidosperma alkaloids.

9. Functional group directed C-H borylation.

10. Total Syntheses of (-)-Deoxoapodine, (-)-Kopsifoline D, and (-)-Beninine.

1. Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.

2. Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.

3. Semi-syntheses and interrogation of indole-substituted Aspidosperma terpenoid alkaloids.