Beilstein J. Org. Chem.2013,9, 2446–2450, doi:10.3762/bjoc.9.282
TES-protected alkene was somewhat lower, probably due to a partial cleavage of the protecting group during the acylation or hydrozirconation step.
Finally, several conditions were studied for the spiroacetalization step. Exposure of the all-TBS protected ketone 17 to moderately strong acids, e.g. the
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Graphical Abstract
Figure 1:
Structure of integramycin (1) and its producing organism, Actinoplanes sp. (Photo: J. Wink, HZI, Mi...
Beilstein J. Org. Chem.2013,9, 1931–1935, doi:10.3762/bjoc.9.228
, Hiratsuka 259-1293, Japan 10.3762/bjoc.9.228 Abstract Symbiodinolide is a polyol marine natural product with a molecular weight of 2860. Herein, a streamlined synthesis of the C79–C97 fragment of symbiodinolide is described. In the synthetic route, a spiroacetalization, a Julia–Kocienski olefination, and a
Sharpless asymmetric dihydroxylation were utilized as the key transformations.
Keywords: Julia–Kocienski olefination; polyol marine natural product; Sharpless asymmetric dihydroxylation; spiroacetalization; symbiodinolide; Findings
A 62-membered polyol marine natural product, symbiodinolide (1, Figure 1
subsequent Sharpless AD [15], wherein the target molecule 8 could be prepared in two steps from the coupling. The carbon framework of 9 could be constructed through the stereoselective spiroacetalization of dihydroxyketone 11.
First, we commenced the stereocontrolled synthesis of aldehyde 20 (Scheme 3