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US 6,096,904 AGranted
Synthetic techniques and intermediates for polyhydroxy, dienyl lactone derivatives
AssigneeThe Trustees of the University of Pennsylvania
InventorsAmos B. Smith, III, Yuping Qiu, Michael Kaufman, Hirokazu Arimoto, David R. Jones, Kaoru Kobayashi, Thomas J. Beauchamp
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Abstract
Synthetic methods for lactone-containing compounds such as the discodermolides are provided, as are compounds which mimic the chemical and/or biological activity thereof, and methods and intermediates useful in their preparation.
Claims3
A process for producing a diene having formula:
- ##STR71## wherein:
- R.sub.1, R.sub.2, R.sub.7, R.sub.8, R.sub.11, and R.sub.12 are, independently, C.sub.1 -C.sub.10 alkyl;
- R.sub.3, R.sub.6 and R.sub.16 are, independently, selected from the group consisting of hydrogen and C.sub.1 -C.sub.6 alkyl;
- R.sub.4, R.sub.9, R.sub.14 and R.sub.15 are, independently, acid labile hydroxyl protecting groups;
- and
- R.sub.25 is an acid stable hydroxyl protecting group;
- comprising contacting a phosphonium salt having formula:
- ##STR72## wherein R.sub.18 is C.sub.1 -C.sub.6 aryl and X is a halogen with a base and a compound having formula:
- ##STR73## for a time and under conditions effective to form said diene.
6 more elements
A compound having one of the following formulas:
- ##STR74## wherein:
- Z.sub.1 and Z.sub.2 are O;
- R.sub.1, R.sub.2, R.sub.7, R.sub.8, R.sub.11, and R.sub.12 are, independently, C.sub.1 -C.sub.10 alkyl;
- R.sub.3 and R.sub.6 are, independently, selected from the group consisting of hydrogen and C.sub.1 -C.sub.6 alkyl;
- R.sub.4, R.sub.9, R.sub.14 and R.sub.15 are, independently, acid labile hydroxyl protecting groups;
- R.sub.5 is C.sub.6 to C.sub.14 aryl;
- R.sub.25 is an acid stable hydroxyl protecting group;
- and
- R.sub.16 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.6 alkyl;
- H or C.sub.1 -C.sub.6 alkyl.
7 more elements
Dependencies are inferred from the claim text.