31756-35-1Relevant academic research and scientific papers
Total Synthesis of β-Bulnesene and 1-Epi-β-bulnesene by Intramolecular Photoaddition
Oppolzer, Wolfgang,Wylie, Robert D.
, p. 1198 - 1203 (1980)
dl-β-Bulnesene (1) and dl-1-epi-β-bulnesene (15) have been synthesized starting from the bromine 4 (Shemes 2 and 3).In the key step 9->10 the bonds of the final product were formed by an interamolecular photoaddition.The synthesis was completed by the fragmentation 12->14 and the Wittig reaction 14->15+1.
Facile approach to the bicyclo[5.3.0]decane ring system; efficient synthesis of (±)-7-epi-β-bulnesene
Ravi Kumar, Jalluri S,O'Sullivan, Michael F,Reisman, Sarah E,Hulford, Catherine A,Ovaska, Timo V
, p. 1939 - 1941 (2002)
An efficient strategy for the rapid construction of the guiane bicyclo[5.3.0]decane ring system from appropriately substituted 4-alkyn-1-ols has been developed. This methodology relies on a MeLi-catalyzed tandem 5-exo-dig cyclization/Claisen rearrangement sequence as the key ring forming step.
Total Synthesis of (+/-)-β-Bulnesene via Intramolecular Cycloaddition of a 2-Substituted 3-Oxidopyrylium
Bromidge, Steven M.,Sammes, Peter G.,Street, Leslie J.
, p. 1725 - 1730 (2007/10/02)
A route to the sesquiterpene (+/-)-β-bulnesene is described which starts with the substituted furan, 2-(1-hydroxy-4-methylhex-5-enyl)furan.Oxidation of the latter generates a precusor of a 2-substituted 3-oxidopyrylium, which undergoes smooth intramolecular cyclisation to generate a highly functionalised perhydroazulene intermediate.Further chemical manipulation of the latter readily generates the desired natural product.In order to control the relative geometry of the pendent-4-methyl group in the target molecule, a method involving the stereoselective reduction of an exocyclic methylene group is employed; the means for introducing such methylene groups are detailed.
Total Synthesis of (+/-)-β-Bulnesene, (+/-)-Cryptofauronol, (+/-)-Fauronyl Acetate, and (+/-)-Valeranone
Sammes, Peter G.,Street, Leslie J.
, p. 666 - 668 (2007/10/02)
A versatile method for the preparation of perhydroazulenes and cis-fused 1-decalones is described and exemplified by the synthesis of the title compounds.
