Total syntheses of (+)-chloropuupehenone and (+)-chloropuupehenol and their analogues and evaluation of their bioactivities

The Journal of Organic Chemistry
Duy H HuaJean-Pierre Perchellet

Abstract

Tetracyclic pyrans (+)-chloropuupehenone (1) and (+)-chloropuupehenol (5) and its C8-R-isomer (+)-3 were synthesized via a one-pot condensation of 1-chloro-2-lithio-3,5,6-tris(tert-butyldimethylsilyloxy)benzene (8) with (4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene-1-carboxaldehyde (7). The major condensation product, (4aS,6aR,12bS)-2H-9,10-bis(tert-butyldimethylsilyloxy)-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-4,4,6a,12b-tetramethyl-benzo[a]xanthene (4), after desilylation provided tetracyclic pyran (+)-(4aS,6aR,12bS)-2H-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-4,4,6a,12b-tetramethyl-benzo[a]xanthene-9,10-diol (3). At a dosage of 42 mg/rat over 8 h, pyran diol 3 inhibited the intestinal absorption of cholesterol by 71% in rats. Tetracyclic pyran 4 was also converted to o-quinone 28, which inhibited cholesteryl ester transfer protein (CETP) activity and L1210 leukemic cell viability with IC(50) values of 31 and 2.4 microM, respectively. Diol (+)-5 inhibited CETP activity with an IC(50) value of 16 microM. The minor condensation product, (4aS,6aS,12bS)-2H-9,10-bis(tert-butyldimethylsilyloxy)-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-4,4,6a,12b-tetramethyl-benzo[a]xanthene (6), was transformed into (+)-5 and ...Continue Reading

References

Jul 7, 2001·Bioscience, Biotechnology, and Biochemistry·H ToshimaT Sassa
Dec 10, 2003·Expert Opinion on Emerging Drugs·Anthony S Wierzbicki

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Citations

Feb 3, 2006·Natural Product Reports·John W BluntMichèle R Prinsep
Apr 17, 2013·Daru : Journal of Faculty of Pharmacy, Tehran University of Medical Sciences·Saeedeh NoushiniAlireza Foroumadi
Feb 8, 2011·The Journal of Steroid Biochemistry and Molecular Biology·Weiqiang LuJin Huang
Oct 3, 2014·The Journal of Organic Chemistry·Ettahir BoulifaEnrique Alvarez-Manzaneda
Oct 27, 2017·Marine Drugs·Beatriz Martínez-PovedaMiguel Ángel Medina
Jan 9, 2009·Angewandte Chemie·Rabea Hennig, Peter Metz
Jul 28, 2005·Natural Product Reports·Braulio M Fraga
Jun 22, 2012·Organic & Biomolecular Chemistry·Song ChenYian Shi
May 11, 2006·Journal of the American Chemical Society·Aleksey V Kurdyumov, Richard P Hsung
Oct 11, 2019·The Journal of Organic Chemistry·Dattatraya Hanumant Dethe, Boda VijayKumar
Oct 17, 2014·The Journal of Organic Chemistry·Zhi-Cong GengXing-Wang Wang
Oct 31, 2017·The Journal of Organic Chemistry·Hong-Shuang WangYan-Chao Wu
Sep 7, 2018·Journal of the American Chemical Society·M Christina White, Jinpeng Zhao

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