𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A diels-alder approach to trans-fused, angularly methylated decalins

✍ Scribed by Steven D. Burke; Tory H. Powner; Masanori Kageyama

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
290 KB
Volume
24
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The title structures can be prepared by Diels-Alder cycloqddition of activated acetylenic or olefinic dienophiles tethered to a proximally-methylated butadiene unit.

The trans-fused decalin system bearing a single angular methyl group is a ubiquitous structural subunit in terpenoid and steroid natural products.

1 Classical synthetic approaches to these subunits have often relied upon the Robinson annulation, followed by reduction of the resultant enone to secure the trans ring junction (eq 1).

2 Obviously, these sequences can readily accommodate certain functionality patterns, while tolerating others less well. A popular complimentary strategy for the construction of six-membered rings is based upon the Diels-Alder reaction, especially in the intramolecular sense. 3 However, questions relating to reactivity and stereoselectivity remain unanswered for certain types of diene-dienophile pairings. Reported herein is a demonstration that the strategy generalized in eq 2 can serve as_ an entry to functionalized, trans-fused decalins which are angularly methylated.

📜 SIMILAR VOLUMES

A Diels–Alder approach to trans-trisbicy
A Diels–Alder approach to trans-trisbicyclo[2.2.1]heptabenzene derivative
✍ Zhong-Qiang Gao; Jun-Fa Wei; Xian-Ying Shi; Jun Yu 📂 Article 📅 2008 🏛 Elsevier Science 🌐 French ⚖ 273 KB

A new route to the synthesis of a trans-tris(bicyclo[2.2.1]hexeno)benzene derivative, using Diels-Alder reaction as critical step, was investigated. The compound with six methoxycarbonyl groups was successfully synthesized in good yield without any organometallic reagents. Some useful by-products fr

ChemInform Abstract: Diels—Alder Reactio
ChemInform Abstract: Diels—Alder Reactions of 4,4-Disubstituted 2-Cyano-2,5-cyclohexadienones. A Facile Approach to the Angularly Substituted cis-Decalin System.
✍ Hsing-Jang Liu; Judy Yip 📂 Article 📅 2000 🏛 John Wiley and Sons ⚖ 36 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Synthesis of steroid precursors. Intramo
Synthesis of steroid precursors. Intramolecular Diels-Alder approach to the trans-hydrindenone system.
✍ Swati A. Bal; Paul Helquist 📂 Article 📅 1981 🏛 Elsevier Science 🌐 French ⚖ 243 KB

Diels-Alder reaction of the 1,3-propanediol-derived ketal of (6E)-2-methyl-1,6,8-nonatrien-3-one produces an approximately 3:l ratio of trans-and cis-hydrindenones. Very recently we have reported a new annulation procedure for the fusion of dihydro-and tetrahydro-naphthalene ring systems onto other