Chemoenzymatic route to optically active dihydroxy cyclopenta [b]naphthalenones; precursors for decalin-based bioactive natural products

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Küçük Resim

Tarih

2017

Dergi Başlığı

Dergi ISSN

Cilt Başlığı

Yayıncı

Pergamon-Elsevier Science Ltd

Erişim Hakkı

info:eu-repo/semantics/closedAccess

Özet

The development of an efficient chemoenzymatic route for the synthesis of optically active dihydroxy cyclopenta[b]naphthalenones; (+)-1,4a-dihydroxy-4a,5,6,7,8,8a,9,9a-octahydro-1H-cyclopenta[b]naphthalen-2(4H)-one (+)-10 and (+)-1,8a-dihydroxy-4a,5,6,7,8,8a,9,9a-octahydro-1H-cydopenta[b]naphthalen-2(4H)-one (+)-11 is described. Different lipases and esterases were tested in the enzymatic hydrolysis of the corresponding acetates (+/-)-4a-hydroxy-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-cyclopenta[b]naphthalen-1-yl acetate (+/-)-8, (+/-)-8a-hydroxy-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydro-1H-cyclopenta[b]naphthalen-1-yl acetate (+/-)-9, CRL (Candida Rugosa Lipase) and PLE (Pig Liver Esterase) were found to be the most effectual enzymes; for (-)-8 by 47% ee with the corresponding dihydroxy; (+)-10 by 98% ee in the presence of CRL; whereas, ()-8 was obtained with 40% ee with the corresponding dihydroxy, (+)-10 with 58% ee in the PLE hydrolysis. It was concluded that CRL was the best biocatalyst for the substrate (+/-)-8. Moreover, enzymatic resolution in the presence of CRL yields, (-)-9 with 46% ee with the corresponding dihydroxy derivative; (+)-11 with 98% ee; however, in the presence of PLE, yields (-)-9 with 36% ee as well as the related dihydroxy derivative; (+)-11 with 49% ee respectively. The study concluded that CRL is the best biocatalyst for compounds (+/-)-8 and (+/-)-9. (C) 2016 Elsevier Ltd. All rights reserved.

Açıklama

Anahtar Kelimeler

Active Dihydroxy Cyclopenta [b]Naphthalenones, Chemoenzymatic Route, Decalin-Based Bioactive Natural Products

Kaynak

Tetrahedron-Asymmetry

WoS Q Değeri

N/A

Scopus Q Değeri

N/A

Cilt

28

Sayı

1

Künye