Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C
2-symmetric building block: a strategy for the synthesis of decanolide natural products
2013 ◽
Vol 9
◽
pp. 2544-2555
◽
Keyword(s):
A Site
◽
Starting from the conveniently available ex-chiral pool building block (R,R)-hexa-1,5-diene-3,4-diol, the ten-membered ring lactones stagonolide E and curvulide A were synthesized using a bidirectional olefin-metathesis functionalization of the terminal double bonds. Key steps are (i) a site-selective cross metathesis, (ii) a highly diastereoselective extended tethered RCM to furnish a (Z,E)-configured dienyl carboxylic acid and (iii) a Ru–lipase-catalyzed dynamic kinetic resolution to establish the desired configuration at C9. Ring closure was accomplished by macrolactonization. Curvulide A was synthesized from stagonolide E through Sharpless epoxidation.
Keyword(s):
2010 ◽
Vol 65
(4)
◽
pp. 445-451
◽
1999 ◽
Vol 64
(26)
◽
pp. 9690-9696
◽
Keyword(s):
Keyword(s):
Keyword(s):
2006 ◽
Vol 3
(2)
◽
pp. 128-134
◽
Keyword(s):