The First Syntheses of (+/-)-SDEF 678 Metabolite and (+/-)-Speciosins A-C

TY - JOUR

T1 - The First Syntheses of (+/-)-SDEF 678 Metabolite and (+/-)-Speciosins A-C

AU - Hookins, Daniel Ritchie

AU - Burns, Alan R.

AU - Taylor, Richard J. K.

PY - 2011/1

Y1 - 2011/1

N2 - The epoxyquinone natural products SDEF 678 metabolite, speciosin A, speciosin B and speciosin C have been prepared for the first time via a short synthetic route based around the palladium-catalysed coupling of a halogen-substituted 1,4-benzoquinone monoketal, a Diels-Alder/retro-Diels-Alder sequence and a diastereoselective epoxidation process.

AB - The epoxyquinone natural products SDEF 678 metabolite, speciosin A, speciosin B and speciosin C have been prepared for the first time via a short synthetic route based around the palladium-catalysed coupling of a halogen-substituted 1,4-benzoquinone monoketal, a Diels-Alder/retro-Diels-Alder sequence and a diastereoselective epoxidation process.

KW - Natural products

KW - Quinones

KW - Speciosins

KW - COUPLING REACTIONS

KW - MANUMYCIN FAMILY

KW - ANTIBIOTICS

KW - MONOKETALS

KW - CATALYSIS

KW - OXIDATION

KW - EFFICIENT

KW - ANALOGS

KW - ROUTE

UR - http://www.scopus.com/inward/record.url?scp=78651345371&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201001402

DO - 10.1002/ejoc.201001402

M3 - Article

SN - 1099-0690

SP - 451

EP - 454

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 3

ER -