(8S)-8α,13β-Dihydroxyserratinane-5-one

CAS No.
5545-99-3
Chemical Name:
(8S)-8α,13β-Dihydroxyserratinane-5-one
Synonyms
Serratinine;(13S)-8α,13-Dihydroxyserratinan-5-one;(8S)-8α,13β-Dihydroxyserratinane-5-one;Serratinin, 7aα,1-Trimethylen-4aβ,5β-(1'β,4'α-dihydroxy-3'α-methyl-tetramethylen)-perhydro-pyrindinon-(7);5H,9H,12H-Indeno[7a,1-h]indolizin-12-one, decahydro-1,4-dihydroxy-2-methyl-, (1S,2S,4S,4aS,11aR,13aS)- (9CI)
CBNumber:
CB82263078
Molecular Formula:
C16H25NO3
Molecular Weight:
279.37
MDL Number:
MOL File:
5545-99-3.mol

(8S)-8α,13β-Dihydroxyserratinane-5-one Properties

Melting point 244-5°C

(8S)-8α,13β-Dihydroxyserratinane-5-one Chemical Properties,Uses,Production

Description

A further alkaloid present in Lycopodium serratum Thunb. vaT. thunbergii Mak. The base crystallizes from Me2CO in colourless prisms and has [α]8D - 27.8° (c 1.44, EtOH). Two non-phenolic hydroxyl groups are present and the alkaloid forms the 8-0-acetate, m.p. 244-5°C; the l3-0-acetate, m.p. 240-2°C and the di-O-acetate, m.p. 1 57-8°C. The tetracyc1ic structure has been proposed on the basis of the mass spectra of the alkaloid and a tentative biogenesis from lycodoline-type alkaloids also proposed.

References

Inubushi et al., Tetrahedron Lett., 1537 (1966)
Mass spectra:
Inubishietal., Tetrahedron, 24,3541 (1968)
Stereochemistry :
Inubushi et al., Tetrahedron Lett., 1551 (1966)
Biosythesis:
Inubushi et aI., Chem. Pharm. Bull. (Tokyo), 16,92 (1968)

(8S)-8α,13β-Dihydroxyserratinane-5-one Preparation Products And Raw materials

Raw materials

Preparation Products

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(13S)-8α,13-Dihydroxyserratinan-5-one (8S)-8α,13β-Dihydroxyserratinane-5-one Serratinine Serratinin, 7aα,1-Trimethylen-4aβ,5β-(1'β,4'α-dihydroxy-3'α-methyl-tetramethylen)-perhydro-pyrindinon-(7) 5H,9H,12H-Indeno[7a,1-h]indolizin-12-one, decahydro-1,4-dihydroxy-2-methyl-, (1S,2S,4S,4aS,11aR,13aS)- (9CI) 5545-99-3