Synthesis of the C(26)-C(42) and C(43)-C(67) pyran-containing fragments of amphidinol 3 via a common pyran intermediate
- PMID: 18205377
- DOI: 10.1021/ol703042q
Synthesis of the C(26)-C(42) and C(43)-C(67) pyran-containing fragments of amphidinol 3 via a common pyran intermediate
Abstract
The pyran-containing fragments 1 and 2 of AM3 have been synthesized from the common pyran intermediate 3. Careful orchestration of the alcohol protecting groups was necessary to facilitate deprotection of alcohol functionality in the presence of the chemically sensitive polyene chain.
Similar articles
-
Synthesis of the C(43)-C(67) fragment of amphidinol 3.Org Lett. 2005 Nov 24;7(24):5509-12. doi: 10.1021/ol052322j. Org Lett. 2005. PMID: 16288543
-
A C-glycosidation approach to the central core of amphidinol 3: synthesis of the c39-c52 fragment.Org Lett. 2005 Apr 28;7(9):1853-6. doi: 10.1021/ol050477l. Org Lett. 2005. PMID: 15844923
-
Synthesis of the C(1)-C(25) fragment of amphidinol 3: application of the double-allylboration reaction for synthesis of 1,5-diols.Org Lett. 2005 Mar 31;7(7):1411-4. doi: 10.1021/ol050250q. Org Lett. 2005. PMID: 15787519
-
Isolation, structural determination and synthetic approaches toward amphidinol 3.Nat Prod Rep. 2014 Apr;31(4):468-88. doi: 10.1039/c3np70062c. Epub 2014 Feb 17. Nat Prod Rep. 2014. PMID: 24531818 Review.
-
Catalytic synthesis of oligoene and enyne derivatives through carbometalation of internal alkynes.Chem Rec. 2008;8(5):326-36. doi: 10.1002/tcr.20158. Chem Rec. 2008. PMID: 18958852 Review.
Cited by
-
INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.Tetrahedron. 2012 Nov 18;68(46):9307-9343. doi: 10.1016/j.tet.2011.12.070. Tetrahedron. 2012. PMID: 23814320 Free PMC article. No abstract available.
-
Karlotoxin synthetic studies: concise synthesis of a C(42-63) B-ring tetrahydropyran fragment.Tetrahedron Lett. 2013 Nov 1;54(48):10.1016/j.tetlet.2013.09.104. doi: 10.1016/j.tetlet.2013.09.104. Tetrahedron Lett. 2013. PMID: 24376284 Free PMC article.
-
A highly convergent synthesis of the C1-C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry.Chem Sci. 2015 Nov 1;6(11):6407-6412. doi: 10.1039/c5sc00814j. Epub 2015 Aug 6. Chem Sci. 2015. PMID: 28757956 Free PMC article.
-
Total synthesis of (-)-CP2-disorazole C1.Org Lett. 2011 Aug 5;13(15):4088-91. doi: 10.1021/ol2015994. Epub 2011 Jul 8. Org Lett. 2011. PMID: 21739942 Free PMC article.
-
Modular ketal-linked prodrugs and biomaterials enabled by organocatalytic transisopropenylation of alcohols.Nat Commun. 2021 Sep 20;12(1):5532. doi: 10.1038/s41467-021-25856-1. Nat Commun. 2021. PMID: 34545089 Free PMC article.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources