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US 5,789,605 AGranted
Synthetic techniques and intermediates for polyhydroxy, dienyl lactones and mimics thereof
AssigneeThe Trustees of the University of Pennsylvania
InventorsAmos B. Smith, III, Yuping Qiu, Michael Kaufman, Hirokaza Arimoto, David R. Jones, Kaoru Kobayashi
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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.
Claims9
A process of producing a diene of the formula:
- ##STR36## comprising contacting a phosphonium salt of the formula ##STR37## with base and an alkylthiol of the formula:
- ##STR38## wherein:
- R.sub.1, R.sub.2, R.sub.3, R.sub.6, R.sub.7, R.sub.8, R.sub.11, R.sub.12 and R.sub.13 are, independently, C.sub.1 -C.sub.10 alkyl;
- X is a halogen;
- Z, Z.sub.1 and Z.sub.2 are, O;
- 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 -C.sub.14 aryl;
- Y is O, S or NR';
- R' and R.sub.16 are, independently, hydrogen or C.sub.1 -C.sub.6 alkyl;
- and
- R.sub.38 is C.sub.6 -C.sub.14 aryl.
8 more elements
A process for producing an alkene of the formula:
- ##STR39## comprising:
- (a) contacting an organometallic reagent of the formula:
- ##STR40## with a vinyl halide of the formula:
- ##STR41## or (b) contacting a vinyl halide of formula:
- ##STR42## with an organometallic compound of formula:
- ##STR43## wherein:
- R.sub.1, R.sub.2, R.sub.3, R.sub.6, R.sub.7 and R.sub.8 are, independently, C.sub.1 -C.sub.10 alkyl;
- M is Li, Cu, Mg, or Zn;
- X is a halogen;
- Z.sub.1 and Z.sub.2 are, O;
- R.sub.4 and R.sub.9 are, independently, acid labile hydroxyl protecting groups;
- R.sub.5 is C.sub.6 -C.sub.14 aryl;
- R' is hydrogen or C.sub.1 -C.sub.6 alkyl;
- and
- R.sub.10 is an acid stable hydroxyl protecting group.
12 more elements
A process of producing a lactone of the formula:
- ##STR44## comprising:
- (a) contacting a diene of the formula ##STR45## with an organometallic compound of the formula:
- ##STR46## or (b) contacting an organometallic compound having formula:
- ##STR47## with a vinyl halide having formula:
- ##STR48## wherein:
- R.sub.1, R.sub.2, R.sub.3, R.sub.6, R.sub.7, R.sub.8, R.sub.11, R.sub.12 and R.sub.13 are, independently, C.sub.1 -C.sub.10 alkyl;
- M is Li, Cu, Mg, or Zn;
- X is a halogen;
- Z, Z.sub.1 and Z.sub.2 are, O;
- 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 -C.sub.14 aryl;
- R' and R.sub.16 are, independently, hydrogen or C.sub.1 -C.sub.6 alkyl;
- and
- R.sub.24 is hydrogen;
- and
- R.sub.25 is hydrogen or an acid stable hydroxyl protecting group.
13 more elements
A process of producing a diene of the formula:
- ##STR49## comprising contacting a phosphonium salt of the formula:
- ##STR50## with base and an alkylthiol of the formula:
- ##STR51## wherein:
- R.sub.6, R.sub.7, R.sub.8, R.sub.11, R.sub.12 and R.sub.13 are, independently, C.sub.1 -C.sub.10 alkyl;
- X is a halogen;
- Z is O;
- R.sub.9, R.sub.14, and R.sub.15 are, independently, acid labile hydroxyl protecting groups;
- Y is O, S or NR';
- R' and R.sub.16 are, independently, hydrogen or C.sub.1 -C.sub.6 alkyl;
- and
- R.sub.18 is C.sub.6 -C.sub.14 aryl.
8 more elements
Dependencies are inferred from the claim text.