11 イワヒメワラビのセスキテルペン類の研究

概要

論文の詳細を見る
Illudoid and seco-illudoid constituents have been isolated from a fern, Hypolepis punctata (Japanese name: Iwahimewarabi). 1). Pterosins, H (1), Z (3) and I (4), were alkyl indanone derivatives with illudane skeleton. The structures were determined by spectral analyses, interconversions and total synthesis. 2). Other natural pterosins, ( )-pterosin D (16) and onitin (18), were derived from pterosin Z (3). 3). Hypacrone (19), a novel seco-illudoid, was a characteristic acrid principle of the fern. The structure was deduced by spectral analyses and by transformation into pterosins on acid treatment. 4). A short-step total synthesis of hypacrone was accomplished. This includes a cross aldol condensation of two major fragments, a cyclopentenone (33) and a 1,3-diketone (23). Dehydration of the aldol product (35) gave 6,7-trans-hypacrone (36), which was equilibrated with 6,7-cis-isomer (natural hypacrone) by sensitized irradiation. Pure cis-hypacrone was isolated by careful chromatography of the cis-trans mixture on neutral alumina.
天然有機化合物討論会の論文
1975-10-01