Gram-scale Synthesis of the A'B'-subunit of Angelmicin B

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2011 Nov 17

PMID 22084899

Citations 5

Authors

Benjamin C Milgram

Brian B Liau

Matthew D Shair

Affiliations

Soon will be listed here.

Abstract

A gram-scale enantiospecific synthesis of the A'B'-subunit of angelmicin B is reported. The synthesis involves a Lewis acid catalyzed contrasteric Diels-Alder reaction and a tandem silyl zincate 1,6-addition/enolate oxidation sequence.

Citing Articles

Asymmetric Synthesis of Nidulalin A and Nidulaxanthone A: Selective Carbonyl Desaturation Using an Oxoammonium Salt.

Ji K, Johnson R, McNeely J, Al Faruk M, Porco Jr J J Am Chem Soc. 2024; 146(7):4892-4902.

PMID: 38319883 PMC: 10922861. DOI: 10.1021/jacs.3c13864.

Synthetic studies directed toward the AB decalin common to HMP-Y1 and hibarimicinone.

Hempel J, Engers D, Sulikowski G Tetrahedron Lett. 2020; 55(13):2157-2159.

PMID: 32855575 PMC: 7449242. DOI: 10.1016/j.tetlet.2014.02.069.

Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group.

Yang Q, Njardarson J Tetrahedron Lett. 2014; 54(51).

PMID: 24391289 PMC: 3878608. DOI: 10.1016/j.tetlet.2013.10.097.

Evolution of an oxidative dearomatization enabled total synthesis of vinigrol.

Yang Q, Draghici C, Njardarson J, Li F, Smith B, Das P Org Biomol Chem. 2013; 12(2):330-44.

PMID: 24258093 PMC: 3901359. DOI: 10.1039/c3ob42191k.

Total syntheses of HMP-Y1, hibarimicinone, and HMP-P1.

Liau B, Milgram B, Shair M J Am Chem Soc. 2012; 134(40):16765-72.

PMID: 22970979 PMC: 3468709. DOI: 10.1021/ja307207q.

References

Kim K, Maharoof U, Raushel J, Sulikowski G . Diverging stereochemical pathways in an intramolecular Diels-Alder reaction determined by dienophile structure. Org Lett. 2003; 5(16):2777-80. DOI: 10.1021/ol034823f. View

Cho S, Fukazawa H, Honma Y, Kajiura T, Hori H, Igarashi Y . Effects of hibarimicins and hibarimicin-related compounds produced by Microbispora on v-Src kinase activity and growth and differentiation of human myeloid leukemia HL-60 cells. J Antibiot (Tokyo). 2002; 55(3):270-8. DOI: 10.7164/antibiotics.55.270. View

Uehara Y, Li P, Fukazawa H, Mizuno S, Nihei Y, Nishio M . Angelmicins, new inhibitors of oncogenic src signal transduction. J Antibiot (Tokyo). 1993; 46(8):1306-8. DOI: 10.7164/antibiotics.46.1306. View

Lee W, Kim K, Sulikowski G . Studies into the stereoselectivity of tartrate-derived dienophiles. Org Lett. 2005; 7(9):1687-9. DOI: 10.1021/ol050105c. View

Ohkata K, Tamura Y, Shetuni B, Takagi R, Miyanaga W, Kojima S . Stereoselectivity control by oxaspiro rings during Diels-Alder cycloadditions to cross-conjugated cyclohexadienones: the syn oxygen phenomenon. J Am Chem Soc. 2004; 126(51):16783-92. DOI: 10.1021/ja047027t. View

Francais A, Urban D, Beau J . Tandem catalysis for a one-pot regioselective protection of carbohydrates: the example of glucose. Angew Chem Int Ed Engl. 2007; 46(45):8662-5. DOI: 10.1002/anie.200703437. View

Hori H, Kajiura T, Igarashi Y, Furumai T, Higashi K, Ishiyama T . Biosynthesis of hibarimicins. I. 13C-labeling experiments. J Antibiot (Tokyo). 2002; 55(1):46-52. DOI: 10.7164/antibiotics.55.46. View

Yokoyama A, Okabe-Kado J, Uehara Y, Oki T, Tomoyasu S, Tsuruoka N . Angelmicin B, a new inhibitor of oncogenic signal transduction, inhibits growth and induces myelomonocytic differentiation of human myeloid leukemia HL-60 cells. Leuk Res. 1996; 20(6):491-7. DOI: 10.1016/0145-2126(96)00014-8. View

Dunn T, Ellis J, Kofink C, Manning J, Overman L . Asymmetric construction of rings A-D of daphnicyclidin-type alkaloids. Org Lett. 2009; 11(24):5658-61. PMC: 2996462. DOI: 10.1021/ol902373m. View

10.

Martin C, Overman L, Rohde J . Total synthesis of (+/-)- and (-)-actinophyllic acid. J Am Chem Soc. 2010; 132(13):4894-906. PMC: 2851836. DOI: 10.1021/ja100178u. View

11.

Kajiura T, FURUMAI T, Igarashi Y, Hori H, Higashi K, Ishiyama T . Signal transduction inhibitors, hibarimicins, A, B, C, D and G produced by Microbispora. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties. J Antibiot (Tokyo). 1998; 51(4):394-401. DOI: 10.7164/antibiotics.51.394. View

12.

Hori H, Igarashi Y, Kajiura T, FURUMAI T, Higashi K, Ishiyama T . Signal transduction inhibitors, hibarimicins A, B, C, D and G produced by Microbispora. II. Structural studies. J Antibiot (Tokyo). 1998; 51(4):402-17. DOI: 10.7164/antibiotics.51.402. View

13.

Narayan S, Roush W . Studies toward the total synthesis of angelmicin B (hibarimicin B): synthesis of a model CD-D' arylnaphthoquinone. Org Lett. 2004; 6(21):3789-92. DOI: 10.1021/ol048436x. View

14.

Kajiura T, Furumai T, Igarashi Y, Hori H, Higashi K, Ishiyama T . Biosynthesis of hibarimicins. II. Elucidation of biosynthetic pathway by cosynthesis using blocked mutants. J Antibiot (Tokyo). 2002; 55(1):53-60. DOI: 10.7164/antibiotics.55.53. View

15.

Trost B, Waser J, Meyer A . Total synthesis of (-)-pseudolaric acid B. J Am Chem Soc. 2008; 130(48):16424-34. PMC: 2698933. DOI: 10.1021/ja806724x. View

16.

Romaine I, Hempel J, Shanmugam G, Hori H, Igarashi Y, Polavarapu P . Assignment and stereocontrol of hibarimicin atropoisomers. Org Lett. 2011; 13(17):4538-41. PMC: 3163008. DOI: 10.1021/ol2017005. View

17.

Lee K, Hoveyda A . Enantioselective conjugate silyl additions to cyclic and acyclic unsaturated carbonyls catalyzed by Cu complexes of chiral N-heterocyclic carbenes. J Am Chem Soc. 2010; 132(9):2898-900. PMC: 2836128. DOI: 10.1021/ja910989n. View

18.

Lambert W, Roush W . Synthesis of the A-B subunit of angelmicin B. Org Lett. 2005; 7(24):5501-4. DOI: 10.1021/ol052321r. View

19.

Li J, Todaro L, Mootoo D . Synthesis of an A'B' Precursor to Angelmicin B: Product Diversification in the Suárez Lactol Fragmentation. European J Org Chem. 2012; 2011(31):6281-6287. PMC: 3383051. DOI: 10.1002/ejoc.201100815. View

20.

Li J, Todaro L, Mootoo D . Synthesis of the AB subunit of angelmicin B through a tandem alkoxy radical fragmentation-etherification sequence. Org Lett. 2008; 10(7):1337-40. PMC: 2692225. DOI: 10.1021/ol703036y. View