Drechslerine D

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Drechslerine D
Category Others
Catalog number BBF-04381
CAS 405157-88-2
Molecular Weight 250.34
Molecular Formula C15H22O3
Purity 95.0%

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Description

Drechslerine D is a metabolite of the algicolous fungus Drechslera dematioidea.

Specification

Synonyms (1S,2R,6R,7R,8S)-1-Methyl-8-(1-hydroxy-1-methylethyl)-11-methylene-4-oxatricyclo[5.3.1.02,6]undecane-5-one; 4,8-Methano-1H-cyclohepta[c]furan-1-one, octahydro-7-(1-hydroxy-1-methylethyl)-4-methyl-9-methylene-, (3aR,4S,7S,8R,8aR)-rel-(-)-
Storage Store at 2-8°C protect from light
IUPAC Name (1R,2R,6R,7S,10S)-10-(2-hydroxypropan-2-yl)-7-methyl-11-methylidene-4-oxatricyclo[5.3.1.02,6]undecan-3-one
Canonical SMILES CC12CCC(C(C1=C)C3C2COC3=O)C(C)(C)O
InChI InChI=1S/C15H22O3/c1-8-11-9(14(2,3)17)5-6-15(8,4)10-7-18-13(16)12(10)11/h9-12,17H,1,5-7H2,2-4H3/t9-,10+,11+,12-,15+/m0/s1
InChI Key DFXRRWWJMJRDNJ-MVIRXUPPSA-N

Properties

Appearance Oily Matter
Boiling Point 384.0±35.0°C at 760 mmHg
Density 1.1±0.1 g/cm3
Solubility Soluble in Ethanol

Reference Reading

1. Total synthesis of the bicyclic marine sesquiterpenoid drechslerine B
Hisahiro Hagiwara, Masakazu Fukushima, Kimihiko Kinugawa, Takuya Matsui, Takashi Hoshi, Toshio Suzuki Nat Prod Commun. 2011 Mar;6(3):311-3.
The total synthesis of the recently isolated bicyclic sesquiterpenoid drechslerine B (2), isolated from the algicolous fungus Drechslera dematioidearare in the marine red alga Liagora viscida, has been achieved, starting from (S)-carvone (8), via an intramolecular aldol reaction and palladium-catalyzed carbon monoxide insertion as key reactions.

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