𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of bicyclo[4.2.0]octan-2-ol, a substructure of solanoeclepin A

✍ Scribed by Minoru Isobe; Supaporn Niyomchon; Chia-Yi Cheng; Anuch Hasakunpaisarn

Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
829 KB
Volume
52
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

A sesterterpenoid solanoeclepin A (1) has a unique structure including a bicyclo[4.2.0]octane substructure, for which a new synthetic methodology is explored particularly to cyclize functionalized cyclobutane rings. An optically active (R)-carvone and a racemic cyclohexenone were each converted into the respective epoxyvinylsulfones, and then subjected to the heteroatom-directed conjugate addition (HAD-CA) by a lithium acetylide nucleophile. The intermediate carbanions from HADCA were used for the following epoxide opening reaction yielding the four-membered carbocyclic products.

📜 SIMILAR VOLUMES

(1RS,2RS,6SR,8SR)-2-Methyl-8-(phenyl­sul
(1RS,2RS,6SR,8SR)-2-Methyl-8-(phenyl­sulfonyl)­bi­cyclo­[4.2.0]­octan-1-ol
✍ Loughlin, Wendy A. ;McCleary, Michelle A. ;Healy, Peter C. 📂 Article 📅 2004 🏛 International Union of Crystallography 🌐 English ⚖ 260 KB

Single-crystal X-ray study T = 295 K Mean '(C±C) = 0.006 A Ê R factor = 0.053 wR factor = 0.174 Data-to-parameter ratio = 20.3 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

(1RS,2SR,6SR,8SR)-2,6-Di­methyl-8-(pheny
(1RS,2SR,6SR,8SR)-2,6-Di­methyl-8-(phenyl­sulfonyl)­bi­cyclo­[4.2.0]­octan-1-ol
✍ Loughlin, Wendy A. ;McCleary, Michelle A. ;Healy, Peter C. 📂 Article 📅 2004 🏛 International Union of Crystallography 🌐 English ⚖ 191 KB

Single-crystal X-ray study T = 295 K Mean '(C±C) = 0.004 A Ê R factor = 0.047 wR factor = 0.131 Data-to-parameter ratio = 19.3 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.