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- Title
Synthese von zwei natürlich vorkommenden Lactonen mit 10gliedrigen Ringen: (±)-Phoracantholid J und I.
- Authors
Gerlach, Hans; Künzler, Peter; Oertle, Konrad
- Abstract
Synthesis of Two Naturally Occurring 10-Membered Ring Lactones: (±)-Phoracantholide J and I Two 10-membered ring lactones 7 and 11 from the metasternal secretion of the eucalypt longicorn Phoracantha synonyma have been synthesized by the following method. Reaction of the dilithium derivative of 4-pentynoic acid ( 3) with 4-tetrahydropyranyloxy-1-pentylbromide ( 2), followed by removal of the protecting group and by esterification with diazomethane, gave methyl 9-hydroxy-4-decynoate ( 4; s. Scheme 1). Partial hydrogenation of the triple bond in 4 with Lindlar palladium catalyst, followed by saponification lead to cis-9-hydroxy-4-decenoic acid ( 6). The 9-hydroxydecanoic acid ( 9) was synthesized by addition of methyl magnesium iodide to methyl 8-formyloctanoate ( 8) followed by saponification (s. Scheme 2). The hydroxy acids 6 and 9 were converted into the S-(2-pyridyl) thioesters and cyclized in dilute benzene solution under the influence of silver ions to yield (±)-phoracantholide J ( 7) and I ( 11) in 74 and 71% yield, respectively.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 4, p1226
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610404