New labdane diterpenoids from the liverwort Scapania undulata

Huneck, S., Connolly, J. D., Harrison, L. J., Joseph, R., Phillips, W. R., Rycroft, D. S., Ferguson, G. and Parvez, M. (1986) New labdane diterpenoids from the liverwort Scapania undulata. Journal of Chemical Research(5), (S) 162-163; (M) 1601–1656.

Abstract

Scapanin A, a diterpenoid isolated from the liverwort Scapania undulata (L.) Dum., and originally named 'scapanin', is shown to be (11S,12Z)-8α,12-epoxy-5α,11-dihydroxylabda-12,14-dien-1-one (4). Nine other new ladbane derivatives, (19) (scapanin B), (24), (29), (35), and (39)–(43), and a novel rearranged labdane (44) (scapanin G) have also been isolated from S. undulata.
The structures were elucidated on the basis of ¹H and ¹³C n.m.r. studies, chemical transformations, and X-ray crystal-structure determinations of the diol (25) and 14,15-dihydroscapanin A (7). The absolute configurations of scapanin A (4) and the alcohol (41) were assigned from the c.d. spectra of their derivatives (14) and (45) respectively.

• Item Type: Articles
• Keywords: Liverwort, natural product chemistry, NMR spectroscopy.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Connolly, Professor Joseph and Rycroft, Dr David
• Authors: Huneck, S., Connolly, J. D., Harrison, L. J., Joseph, R., Phillips, W. R., Rycroft, D. S., Ferguson, G., and Parvez, M.
• Subjects: Q Science > QD Chemistry; Q Science > QK Botany
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of Chemical Research
• Publisher: The Royal Society of Chemistry
• ISSN: 0308-2342