𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Total Synthesis of Angucyclines, 4. Synthesis ofrac-Tetrangomycin

✍ Scribed by Krohn, Karsten ;Khanbabaee, Karamali

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
458 KB
Volume
1994
Category
Article
ISSN
0947-3440

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The synthesis of racemic tetrangomycin (11) is reported. In the key step the hexahydrobenz[α]anthraquinone 8 is generated in a regioselective Diels‐Alder reaction of diene 5 with bromonaphthoquinone 7. The conversion of 8 into 11 involves only three operations: treatment with diethyl ether–boron trifluoride, hydrogen peroxide and photooxygenation.

📜 SIMILAR VOLUMES

Synthetic angucyclines, 3. First total s
Synthetic angucyclines, 3. First total synthesis ofrac-rabelomycin by Diels-Alder reaction
✍ Krohn, Karsten ;Khanbabaee, Karamali ;Flörke, Ulrich ;Jones, Peter G. ;Chrapkows 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 English ⚖ 775 KB

## Abstract Conjugate addition of the 2‐siloxydienes 5a and 5b to juglone (4a) or 3‐chlorojuglone (4b) affords the products 6–8a and 8b, respectively. The reaction of 4a with furan 10 yields the substitution product 11, which is converted to the 5‐hydroxybutenolide 12 by treatment with MCPBA. Hexam

Total synthesis of angucyclines, 7. Hydr
Total synthesis of angucyclines, 7. Hydroaromatic angucyclines of the SF-2315 type
✍ Krohn, Karsten ;Khanbabaee, Karamali ;Jones, Peter G. 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 622 KB

## Abstract Osmylation of the Diels‐Alder adduct 3 afforded the __cis__‐diol 4, which was dehydrated by acid treatment to the phenol 6. Reaction with tetrafluoroboric acid converted the diol 4 by intramolecular acyl shift into the acetate 7. The relative stereochemistry of 7 was determined by singl

Total Synthesis ofrac-Silandrin, an Anti
Total Synthesis ofrac-Silandrin, an Antihepatotoxic Flavanolignan
✍ Antus, Sándor ;Baitz-Gács, Eszter ;Gottsegen, Agnes ;Kovács, Tibor ;Szunyog, Józ 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 509 KB

## Abstract The first synthesis of racemic silandrin (__rac__‐1), which shows significant antihepatotoxic activity, has been accomplished via the key intermediate 9 prepared from the readily available starting materials caffeic acid ethyl ester (4) and coniferyl alcohol (5).

Total Synthesis of Angucyclines, 1. – Sy
Total Synthesis of Angucyclines, 1. – Synthesis of a Daunomycinone–Rabelomycin Hybrid
✍ Krohn, Karsten ;Ballwanz, Frank ;Baltus, Wolfgang 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 339 KB

## Abstract The synthesis of the racemic angucyclinone hybrid 3 which combines the structural features of rabelomycin (1) and daunomycinone (2) is described. Key steps are the cyclization of the bromide 6b by a Marshalk‐type reaction to yield the angular skeleton 7b, introduction of the tertiary hy