✦ LIBER ✦

Total Synthesis of (+)-Machaeriols B and C and of Their Enantiomers with a Cannabinoid Structure

✍ Scribed by Hee Jin Lee; Yong Rok Lee; Sung Hong Kim

Publisher: John Wiley and Sons
Year: 2009
Tongue: German
Weight: 200 KB
Volume: 92
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200900014

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

An efficient and concise synthesis of the biologically interesting (+)‐machaeriol B (2) and its enantiomer 5 was accomplished from O‐phenylhydroxylamine (7) in four steps (Scheme 2). In addition, the first total synthesis of natural (+)‐machaeriol C (3) and its enantiomer 6 was achieved from the readily available ester 15 in eight steps (Scheme 4). The key strategies in the syntheses of 2 and 5 involved benzofuran formation through a [3,3]‐sigmatropic rearrangement and trans‐hexahydrodibenzopyran formation by a domino aldol‐type/hetero‐Diels–Alder reaction. In the case of 3 and 6, the key steps were stilbene formation by a Horner–Wadsworth–Emmons reaction and trans‐hexahydrodibenzopyran formation by domino reactions.

📜 SIMILAR VOLUMES

ChemInform Abstract: Total Synthesis of

ChemInform Abstract: Total Synthesis of Tryprostatin A and B as well as Their Enantiomers.

✍ S. ZHAO; T. GAN; P. YU; J. M. COOK 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 2 views

Total Synthesis of (+)-Machaeriol D with

Total Synthesis of (+)-Machaeriol D with a Key Regio- and Stereoselective SN2′ Reaction

✍ Qiaoling Wang; Qinggang Huang; Bo Chen; Jiangping Lu; Hui Wang; Xuegong She; Xin 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 English ⚖ 123 KB 👁 2 views

Total Synthesis of (+)-Machaeriol D with

Total Synthesis of (+)-Machaeriol D with a Key Regio- and Stereoselective SN2′ Reaction

✍ Qiaoling Wang; Qinggang Huang; Bo Chen; Jiangping Lu; Hui Wang; Xuegong She; Xin 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 English ⚖ 123 KB 👁 2 views

Total Synthesis of (+)-Machaeriol D (I)

Total Synthesis of (+)-Machaeriol D (I) with a Key Regio- and Stereoselective SN2′ Reaction.

✍ Qiaoling Wang; Qinggang Huang; Bo Chen; Jiangping Lu; Hui Wang; Xuegong She; Xin 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 10 KB 👁 2 views

A Practical Total Synthesis of Both Enan

A Practical Total Synthesis of Both Enantiomers of Epoxyquinols A (I) and B (II).

✍ Mitsuru Shoji; Satoshi Kishida; Mitsuhiro Takeda; Hideaki Kakeya; Hiroyuki Osada 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 80 KB 👁 2 views

Total Synthesis of Coralloidolides A, B,

Total Synthesis of Coralloidolides A, B, C, and E

✍ Thomas J. Kimbrough; Paul A. Roethle; Peter Mayer; Dirk Trauner 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 305 KB 👁 1 views