Rhodium-catalyzed Asymmetric Enyne Cycloisomerization of Terminal Alkynes and Formal Total Synthesis of (-)-platensimycin

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2009 Jul 17

PMID 19606433

Citations 9

Authors

K C Nicolaou

Ang Li

Shelby P Ellery

David J Edmonds

Affiliations

Soon will be listed here.

Citing Articles

Short Enantioselective Formal Synthesis of (-)-Platencin.

Defieber C, Mohr J, Grabovyi G, Stoltz B Synthesis (Stuttg). 2019; 50(22):4359-4368.

PMID: 31061542 PMC: 6498846. DOI: 10.1055/s-0037-1610437.

Formal (4+1)-Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides.

Roiser L, Zielke K, Waser M Synthesis (Stuttg). 2018; 50(20):4047-4054.

PMID: 30297974 PMC: 6173290. DOI: 10.1055/s-0037-1610268.

A brief history of antibiotics and select advances in their synthesis.

Nicolaou K, Rigol S J Antibiot (Tokyo). 2017; 71(2):153-184.

PMID: 28676714 DOI: 10.1038/ja.2017.62.

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Brill Z, Condakes M, Ting C, Maimone T Chem Rev. 2017; 117(18):11753-11795.

PMID: 28293944 PMC: 5638449. DOI: 10.1021/acs.chemrev.6b00834.

Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization.

Trost B, Ryan M, Rao M Beilstein J Org Chem. 2016; 12:1136-52.

PMID: 27559366 PMC: 4979649. DOI: 10.3762/bjoc.12.110.

References

Wender P, Haustedt L, Lim J, Love J, Williams T, Yoon J . Asymmetric catalysis of the [5 + 2] cycloaddition reaction of vinylcyclopropanes and pi-systems. J Am Chem Soc. 2006; 128(19):6302-3. DOI: 10.1021/ja058590u. View

Nicolaou K, Chen J, Edmonds D, Estrada A . Recent advances in the chemistry and biology of naturally occurring antibiotics. Angew Chem Int Ed Engl. 2009; 48(4):660-719. PMC: 2730216. DOI: 10.1002/anie.200801695. View

Furstner A, Majima K, Martin R, Krause H, Kattnig E, Goddard R . A cheap metal for a "noble" task: preparative and mechanistic aspects of cycloisomerization and cycloaddition reactions catalyzed by low-valent iron complexes. J Am Chem Soc. 2008; 130(6):1992-2004. DOI: 10.1021/ja0777180. View

Nicolaou K, Li A, Edmonds D . Total synthesis of platensimycin. Angew Chem Int Ed Engl. 2006; 45(42):7086-90. DOI: 10.1002/anie.200603892. View

Trost B . On inventing reactions for atom economy. Acc Chem Res. 2002; 35(9):695-705. DOI: 10.1021/ar010068z. View

Lei A, He M, Zhang X . Rh-catalyzed kinetic resolution of enynes and highly enantioselective formation of 4-alkenyl-2,3-disubstituted tetrahydrofurans. J Am Chem Soc. 2003; 125(38):11472-3. DOI: 10.1021/ja0351950. View

Trost B, Frederiksen M, Rudd M . Ruthenium-catalyzed reactions--a treasure trove of atom-economic transformations. Angew Chem Int Ed Engl. 2005; 44(41):6630-66. DOI: 10.1002/anie.200500136. View

Kressierer C, Muller T . Novel three-component reactions based on a Heck carbopalladation/cyclization domino reaction. Angew Chem Int Ed Engl. 2004; 43(44):5997-6000. DOI: 10.1002/anie.200461134. View

Liu F, Liu Q, He M, Zhang X, Lei A . Rh-catalyzed highly enantioselective formation of functionalized cyclopentanes and cyclopentanones. Org Biomol Chem. 2007; 5(21):3531-4. DOI: 10.1039/b712396e. View

10.

Tiefenbacher K, Mulzer J . Synthesis of platensimycin. Angew Chem Int Ed Engl. 2008; 47(14):2548-55. DOI: 10.1002/anie.200705303. View

11.

Nicolaou K, Gray D, Montagnon T, Harrison S . Oxidation of silyl enol ethers by using IBX and IBX.N-oxide complexes: a mild and selective reaction for the synthesis of enones. Angew Chem Int Ed Engl. 2002; 41(6):996-1000. DOI: 10.1002/1521-3773(20020315)41:6<996::aid-anie996>3.0.co;2-i. View

12.

Lei A, He M, Zhang X . Highly enantioselective syntheses of functionalized alpha-methylene-gamma-butyrolactones via Rh(I)-catalyzed intramolecular Alder ene reaction: application to formal synthesis of (+)-pilocarpine. J Am Chem Soc. 2002; 124(28):8198-9. DOI: 10.1021/ja020052j. View

13.

Cao , Zhang . The First Highly Enantioselective Rh-Catalyzed Enyne Cycloisomerization This work was supported by an NIH grant, a Dreyfus Teaching-Scholar Award, and a DuPont Young Faculty Award. P.C. acknowledges the Dalalian Fellowship from the Department of.... Angew Chem Int Ed Engl. 2000; 39(22):4104-4106. DOI: 10.1002/1521-3773(20001117)39:22<4104::aid-anie4104>3.0.co;2-x. View

14.

Furstner A, Martin R, Majima K . Cycloisomerization of enynes catalyzed by iron(0)-ate complexes. J Am Chem Soc. 2005; 127(35):12236-7. DOI: 10.1021/ja0532739. View

15.

Lei A, Waldkirch J, He M, Zhang X . Highly enantioselective cycloisomerization of enynes catalyzed by rhodium for the preparation of functionalized lactams. Angew Chem Int Ed Engl. 2002; 41(23):4526-9. DOI: 10.1002/1521-3773(20021202)41:23<4526::AID-ANIE4526>3.0.CO;2-K. View

16.

Hatano M, Mikami K . Highly enantioselective quinoline synthesis via ene-type cyclization of 1,7-enynes catalyzed by a cationic BINAP-palladium(II) complex. J Am Chem Soc. 2003; 125(16):4704-5. DOI: 10.1021/ja0292748. View

17.

Lei A, He M, Wu S, Zhang X . Highly enantioselective Rh-catalyzed intramolecular Alder-ene reactions for the syntheses of chiral tetrahydrofurans. Angew Chem Int Ed Engl. 2002; 41(18):3457-60. DOI: 10.1002/1521-3773(20020916)41:18<3457::AID-ANIE3457>3.0.CO;2-3. View

18.

Nicolaou K, Edmonds D, Li A, Tria G . Asymmetric total syntheses of platensimycin. Angew Chem Int Ed Engl. 2007; 46(21):3942-5. DOI: 10.1002/anie.200700586. View