A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.
A simple device consisting of two ion-exchange columns, two alumina-based filters, and a pump (Figure 1) was assembled to form the C8-C14 polycyclic ring system present in the halichondrin B class of marine natural products. The effectiveness of this device was tested for three substrates. In each case, the desired polycyclic ketal 3, 5, or 7 was obtained almost quantitatively in a single operation.
Namba
Kosuke
K
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Jun
Hyuk-Sang
HS
Kishi
Yoshito
Y
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D018942:Macrolides; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D000095662:Polyether Polyketides
D000447:Aldehydes; D004988:Ethers, Cyclic; D007659:Ketones; D018942:Macrolides; C070519:halichondrin B; D000095662:Polyether Polyketides