Enantioselective Total Synthesis of (+)-Vittatalactone

1.

Enantioselective Total Synthesis of (+)-Vittatalactone
Агрегационный феромон
Полосатый жук-огурец
Acalymma vittatum

2.

Retrosynthetic analysis of (+)-vittatalactone (1)

3.

Synthesis of alcohol 4

4.

Synthesis of (+)-vittatalactone (1)

5.

Synthesis of (+)-vittatalactone (1)
Pinnick oxidation

6.

A 12-membered to a strained 11-membered ring: first stereoselective
total synthesis of (-)-asteriscunolide C
Asteriscus aquaticus
Гумулен

7.

Retrosynthesis of asteriscunolides C and D
(Ring-closing metathesis)

8.

Synthesis of allyl alcohol fragment 11

9.

Synthesis of acid fragment 10
A. Erkkilä and P. M. Pihko, J. Org. Chem., 2006, 71, 2538

10.

Attempted intramolecular HWE-cyclization
Yamaguchi esterification

11.

Synthesis of clavulactone analogues 26 and 27

12.

An unsaturation to the lactone motif