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Literature DB >> 18362952

An iodoetherification-dehydroiodination strategy for the synthesis of complex spiroketals from dihydroxyalkene precursors.

K A Tony¹, Xiaohua Li, Darrin Dabideen, Jialiang Li, David R Mootoo.

Abstract

Dihydroxyalkenes or their monoprotected alcohol derivatives are transformed to 5,5- and 5,6-spiroketals through a sequence involving an initial iodocyclization, followed by a silver triflate mediated spiroketalization step on the derived hydroxy-iodoether.

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Year: 2008 PMID： 18362952 PMCID： PMC3395191 DOI： 10.1039/b719247a

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

22 in total

1. Combinatorial synthesis of natural product-like molecules using a first-generation spiroketal scaffold.

Authors: Bheemashankar A Kulkarni; Gregory P Roth; Emil Lobkovsky; John A Porco
Journal: J Comb Chem Date: 2002 Jan-Feb

2. Diastereoselective synthesis of the C(17)-C(28) fragment (the C-D spiroketal unit) of spongistatin 1 (altohyrtin A) via a kinetically controlled iodo-spiroketalization reaction.

Authors: Edward B Holson; William R Roush
Journal: Org Lett Date: 2002-10-17 Impact factor: 6.005

3. Asymmetric solid-phase synthesis of 6,6-spiroketals.

Authors: Okram Barun; Stefan Sommer; Herbert Waldmann
Journal: Angew Chem Int Ed Engl Date: 2004-06-14 Impact factor: 15.336

4. Synthesis of bistramide A.

Authors: Alexander V Statsuk; Dong Liu; Sergey A Kozmin
Journal: J Am Chem Soc Date: 2004-08-11 Impact factor: 15.419

5. Synthesis of the C16-C35 fragment of integramycin using olefin hydroesterification as a linchpin reaction.

Authors: Lijun Wang; Paul E Floreancig
Journal: Org Lett Date: 2004-02-19 Impact factor: 6.005

6. Synthesis of the C11-C23 fragment of spirastrellolide A. A ketal-tethered RCM approach to the construction of spiroketals.

Authors: Jia Liu; Richard P Hsung
Journal: Org Lett Date: 2005-05-26 Impact factor: 6.005

An iodoetherification-dehydroiodination strategy for the synthesis of complex spiroketals from dihydroxyalkene precursors.

1. Combinatorial synthesis of natural product-like molecules using a first-generation spiroketal scaffold.

2. Diastereoselective synthesis of the C(17)-C(28) fragment (the C-D spiroketal unit) of spongistatin 1 (altohyrtin A) via a kinetically controlled iodo-spiroketalization reaction.

3. Asymmetric solid-phase synthesis of 6,6-spiroketals.

4. Synthesis of bistramide A.

5. Synthesis of the C16-C35 fragment of integramycin using olefin hydroesterification as a linchpin reaction.

6. Synthesis of the C11-C23 fragment of spirastrellolide A. A ketal-tethered RCM approach to the construction of spiroketals.

7. Total synthesis and confirmation of the revised structures of azaspiracid-2 and azaspiracid-3.

8. Stereocontrolled synthesis of spiroketals via a remarkable methanol-induced kinetic spirocyclization reaction.

9. Asymmetric total synthesis of spongistatins 1 and 2.

10. Synthesis of cis- and trans-2,5-disubstituted tetrahydrofurans by a tandem dihydroxylation-SN2 cyclization sequence.

1. Olefin metathesis-iodoetherification-dehydroiodination strategy for spiroketal subunits of polyether antibiotics.

Review 2. Recent synthetic approaches toward non-anomeric spiroketals in natural products.