119650-41-8Relevant academic research and scientific papers
Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products
Zamarija, Ivica,Marsh, Benjamin J.,Magauer, Thomas
supporting information, p. 9221 - 9226 (2021/11/30)
Herein, we describe a two-step ring expansion of 1-indanones to afford 2-chloro/bromo-1-naphthols (32 examples). The developed method shows broad functional group tolerance, benefits from mild reaction conditions, and enables rapid access to the tetracyclic core of gilvocarcin natural products. The orthogonally functionalized products allow for selective postmodifications as exemplified in the total synthesis of defucogilvocarcin M. For the selective oxidation of the chromene, a mild and regioselective oxidation protocol (DDQ and TBHP) was developed.
Total synthesis of jadomycin A and a carbasugar analogue of jadomycin B
Shan, Mingde,Sharif, Ehesan U.,O'Doherty, George A.
supporting information; experimental part, p. 9492 - 9495 (2011/02/22)
One's trash is another one's treasure: The first syntheses of jadomycin A and the carbasugar analogue of jadomycin B have been achieved in 6 and 20 longest linear steps, respectively. The key ring system of the aglycone was prepared by a 6π-electron elect
C-Glycosylation of tri-O-benzyl-2-deoxy-D-glucose: Synthesis of naphthyl-substituted 3,6-dioxabicyclo[3.2.2]nonanes
Brimble,Brenstrum
, p. 1612 - 1623 (2007/10/03)
The syntheses of naphthol 7, naphthol 8, naphthol 11 and naphthol 12 are described, starting from juglone 13. C-Glycosylation of naphthol 8 with benzyl-protected glycosyl donor 10 using trimethylsilyl trifluoromethanesulfonate and silver perchlorate or boron trifluoride-diethyl ether affords rearranged product 36 in which the glycosyl donor has undergone an unusual 1,6-hydride shift. Use of the corresponding naphthol 12 as the glycosyl acceptor under the same conditions affords the expected C-glycoside 34. Use of the naphthol 7 and naphthol 11 affords predominantly rearranged products 35 and 37 respectively, albeit in much lower yield than the reactions using the corresponding bromonaphthols. The study described herein establishes that introduction of an acetyl group to C-3, as in C-glycosylnaphthoquinone 4, as required for conversion to analogues of medermycin 1 such as 3, necessitates that the C-glycosylation step be effected before regioselective introduction of the acetyl group.
Synthesis of naphthyl C-glycosides of rearranged tri-O-benzyl-2-deoxy-D- glucose
Brimble, Margaret A.,Brenstrum, Timothy J.
, p. 1107 - 1110 (2007/10/03)
C-Glycosylation of 3-bromonaphthol 4 with benzyl-protected glycosyl donor 19 afforded rearranged bicyclic acetal 24 in which the glycosyl donor had undergone an unusual 1,6-hydride shift. Use of the regioisomeric 2- bromonaphthol 6 with the same glycosyl donor 19 afforded the expected β-C- glycoside 22. (C) 2000 Elsevier Science Ltd.
A Synthetic Approach to (+)-Dioncophylline C
Gable, Robert W.,Martin, Robyn L.,Rizzacasa, Mark A.
, p. 2013 - 2022 (2007/10/02)
In a synthetic approach to (+)-dioncophylline C (1), a coupling between the chiral oxazoline (3) and the Grignard reagent obtained from bromide (4) gave the major biaryl (5) and the minor biaryl (12) in good yield and high diastereoselectivity (yield 70pe
