EurekaMag.com logo
+ Translate

Synthesis of the optically active hexahydrobenzofuran nucleus of the avermectins


, : Synthesis of the optically active hexahydrobenzofuran nucleus of the avermectins. Tetrahedron Letters 29(28): 3415-3418

A preparation of an optically pure hexahydrobenzofuranone subunit common to the milbemycin-avermectin macrocycles is reported for 1,4-anhydrosorbitol.

Accession: 001962639

DOI: 10.1016/0040-4039(88)85177-3

Download PDF Full Text: Synthesis of the optically active hexahydrobenzofuran nucleus of the avermectins


Submit PDF Full Text

No spam - Every submission is manually reviewed

Due to poor quality, we do not accept files from Researchgate

Submitted PDF Full Texts will always be free for everyone
(We only charge for PDFs that we need to acquire)

Select a PDF file:
Close
Close

Related references

Michael T.C.immins; John G.L.ver, 1986: Synthesis of the hexahydrobenzofuran subunit of the milbemycins and the avermectins. A synthesis of the hexahydrobenzofuran subunit of milbemycins J and K has been accomplished in 17 steps from 4-methyl-1,4-pentadienol.

Ferezou J.P.; Julia M.; L.Y.; Liu L.W.; Pancrazi A., 1990: Enantioselective synthesis of the hexahydrobenzofuran part of avermectins. An asymmetric synthesis of the southern C1-C9 bicyclic fragment of avermectins has been developed in 13 steps from a propargyl ether and 2-methylhept-2-en-6-one via an acyclic diester intermediate [dimethyl (2R,3S)-3,4-isopropylidenedioxy-4-methyl...

Lee K C.; W.J.C.C.; Yen K F.; Uang B J., 1990: Enantioselective synthesis of the hexahydrobenzofuran subunit of the avermectins and the milbemycins. Tetrahedron Letters 31(25): 3563-3566

Parsons, P., J.; Willis, P.; Eyley, S.C., 1992: A synthesis of the hexahydrobenzofuran portion of the avermectins: I. Model studies. A tandem radical cyclization has been used to construct a model for the synthesis of the hexahydrobenzofuran moiety present in the avermectins.

Barrett, A.; Capps, N., 1986: Synthetic approaches to the avermectins: studies on the hexahydrobenzofuran unit. The condensation reaction of 2-lithio-2-lithio-oxymethyl-1,3-dithiane with an epoxy-ketone is used as the key step in a novel approach to the avermectin southern hexahydrobenzofuran unit.

Narukawa, Y.; Juneau, K.N.; Snustad, D.; Miller, D.B.; Hegedus, L.S., 1992: Synthesis of optically active beta-lactams by the photolytic reaction of imines with optically active chromium carbene complexes: 2. Synthesis of 1-carbacephalothin and 3-ANA relays. A relay (3) to optically active 1-carbacephalothin (4) was prepared in modest yield with high stereoselectivity by the photochemical reaction of optically active chromium carbene complex 1 with functionalized imine 2. In contrast, the photochemica...

Ireland R.E.; Obrecht D.M., 1986: Diels alder approach to highly functionalized tertiary alpha hydroxyketones a novel route to the hexahydrobenzofuran portion of the avermectins and milbemycins. A highly regio- and stereoselective Diels-Alder reaction between dienophiles of type I and dienes of type II (Scheme 1) gives rise to Diels-Alder adducts of type III. Upon treatment with BF3 .cntdot. Et2O, these adducts are smoothly converted into...

Nokami J.; Mandai T.; Nishimura A.; Takeda T.; Wakabayashi S.; Kunieda N., 1986: Synthesis of optically active 4 hydroxyalk 2 ene nitriles reaction of optically active 2 p chlorophenylsulfinylacetonitrile with aldehydes in the presence of piperidine in acetonitrile. Tetrahedron Letters 27(42): 5109-5112

Hirrlinger, B.; Stolz, A.; Knackmuss, H.J.achim, 2001: Enzymatic synthesis of optically active hydroxamic acids and their conversion to optically active primary amines by a lossen rearrangement. A method is described for the preparation of optically active hydroxamic acids of the general formula ##STR1## wherein R1, R2 and R3 are different and are a cyclic or linear, aliphatic or aromatic, substituted or unsubstituted hydrocarbon radical...

Hegedus L.S.; Imwinkelried R.; Alarid Sargent M.; Dvorak D.; Satoh Y., 1990: Synthesis of optically active beta lactams by the photolytic reaction of imines with optically active chromium carbene complexes. Optically active chromium carbene complexes utilizing (S)-valine- and (R)-phenylglycine-derived chiral auxillaries were synthesized and subjected to photolytic reaction with a number of imines. Optically active .beta.-lactams were produced in good...