35 鎖状イソプレノイドの末端位修飾を利用するフラノテルペンの合成

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概要

• 論文の詳細を見る

• A combination of regioselective sulfenylation of monoterpenoids (11) furnishing terminal allylic sulfides (12) and thermal elimination of phenylsulfenic acid from the corresponding sulfoxides constitutes a general method for conversion of the isopropylidene terminus of monoterpenoids to the 1,3-diene system (14). The general applicability of the method was demonstrated on the monoterpenoids possessing various functional groups. Several 1,3-dienes (14) thus obtained were transformed to furan derivatives (16) by photosensitized oxygenation followed by dehydration. Furans (16) were utilized effectively for syntheses of cyclic and acyclic furanoterpenes. Optically active natural evodone (2) was synthesized and the configuration of the asymmetric center was determined as (R) by cyclization of the optically active 4-(2-furyl)-butanoic acid derivative (19) which was prepared from R-(+)-citrone-llic acid (17) by the above sequence of reactions. The analogous cyclization of the furan derivative (16d) gave 6,7-dihydro-4(5H)-benzofuranone derivative (10), a synthetic key intermediate for linderalactone (8) and curzerenone (9). Carbon-carbon coupling of the furan derivative (16e) bearing a terminal allylic sulfonyl group with 3-furylmethyl bromide and trans 4-benzyloxy-2-methyl-2-butenyl bromide followed by reductive desulfonation and deprotection provided dehydrolasiosperman W and a synthetic intermediate (26) for plera-plysillin-2 (4) respectively.

• 天然有機化合物討論会の論文
• 1981-09-10

著者

• 正木 幸雄

  岐薬大

• 佐久間 和彦

  岐薬大

• 橋本 謹治

  岐薬大

• 鍛治 健司

  岐薬大

関連論文

• 35 鎖状イソプレノイドの末端位修飾を利用するフラノテルペンの合成
• 3 生理活性な鎖状減成テルペノイドの新しい位置及び立体選択的合成
• 71 C_2対称性を利用する酒石酸の新しい変換法とその光学活性天然物合成への応用

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