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Pheromone synthesis, CXXVII. A new synthesis of the enantiomers of grandisol and lineatin

✍ Scribed by Mori, Kenji ;Nagano, Eiki

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
429 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The enantiomers of grandisol (1) and lineatin (2) have been synthesized by resolving the key (±)‐hydroxy ether (±)‐7 as its diastereomeric esters 8 and 8′ with (−)‐camphanic acid.

📜 SIMILAR VOLUMES

Pheromone Synthesis, CXXXVII. A New Synt
Pheromone Synthesis, CXXXVII. A New Synthesis of (+)-Grandisol
✍ Mori, Kenji ;Fukamatsu, Kunio 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 521 KB

## Abstract The natural and (+)‐enantiomer of grandisol [1, (1__R__,2__S__)‐(+)‐2‐isopropenyl‐1‐methylcyclobutaneethanol] has been synthesized from (__R__)‐(—)‐carvone (2) by employing the intramolecular alkylation of 8 to give 9 as the key step.

A New Stereoselective Synthesis of Grand
A New Stereoselective Synthesis of Grandisol
✍ Langer, Klaus ;Mattay, Jochen ;Heidbreder, Andreas ;Möller, Manfred 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 370 KB

## Abstract Grandisol (10) is stereoselectively synthesized in 9 steps, starting from commercially available 3‐methyl‐3‐buten‐1‐ol (1). The key step of the synthesis is the Cu(I)‐catalyzed [2 + 2]‐photocycloaddition of 3 to 4a or 4b. Moreover, solvent effects on the __endo/exo__ product ratio of th