This is apparently a limitation of MKMapView.
The workaround is to split the +/- 180 transition into the "eastern" and "western" parts.
For a trip around the world (finish == start), you can place the "western" part of the intersection in front of the polyline.
For instance:
CLLocationCoordinate2D newYorkCoord = CLLocationCoordinate2DMake(40.7141667, -74.0063889);
CLLocationCoordinate2D londonCoord = CLLocationCoordinate2DMake(51.5, -0.116667);
CLLocationCoordinate2D japanCoord = CLLocationCoordinate2DMake(36, 138);
CLLocationCoordinate2D sanFranciscoCoord = CLLocationCoordinate2DMake(37.775, -122.4183333);
CLLocationCoordinate2D japanToSFMidpointEast;
japanToSFMidpointEast.latitude = (japanCoord.latitude + sanFranciscoCoord.latitude)/2.0;
japanToSFMidpointEast.longitude = 180;
CLLocationCoordinate2D japanToSFMidpointWest;
japanToSFMidpointWest.latitude = japanToSFMidpointEast.latitude;
japanToSFMidpointWest.longitude = -180;
int pointsCount = 6;
CLLocationCoordinate2D *points = malloc(pointsCount * sizeof(CLLocationCoordinate2D));
points[0] = japanToSFMidpointWest;
points[1] = sanFranciscoCoord;
points[2] = newYorkCoord;
points[3] = londonCoord;
points[4] = japanCoord;
points[5] = japanToSFMidpointEast;
MKPolyline *polyline = [MKPolyline polylineWithCoordinates:points count:pointsCount];
[mapView addOverlay:polyline];
free(points);
points = NULL;
(!= ), .
SF:
CLLocationCoordinate2D japanCoord = CLLocationCoordinate2DMake(36, 138);
CLLocationCoordinate2D sanFranciscoCoord = CLLocationCoordinate2DMake(37.775, -122.4183333);
CLLocationCoordinate2D japanToSFMidpointEast;
japanToSFMidpointEast.latitude = (japanCoord.latitude + sanFranciscoCoord.latitude)/2.0;
japanToSFMidpointEast.longitude = 180;
CLLocationCoordinate2D japanToSFMidpointWest;
japanToSFMidpointWest.latitude = japanToSFMidpointEast.latitude;
japanToSFMidpointWest.longitude = -180;
int eastPointsCount = 2;
CLLocationCoordinate2D *eastPoints = malloc(eastPointsCount * sizeof(CLLocationCoordinate2D));
eastPoints[0] = japanCoord;
eastPoints[1] = japanToSFMidpointEast;
MKPolyline *eastPolyline = [MKPolyline polylineWithCoordinates:eastPoints count:eastPointsCount];
[mapView addOverlay:eastPolyline];
free(eastPoints);
eastPoints = NULL;
int westPointsCount = 2;
CLLocationCoordinate2D *westPoints = malloc(westPointsCount * sizeof(CLLocationCoordinate2D));
westPoints[0] = japanToSFMidpointWest;
westPoints[1] = sanFranciscoCoord;
MKPolyline *westPolyline = [MKPolyline polylineWithCoordinates:westPoints count:westPointsCount];
[mapView addOverlay:westPolyline];
free(westPoints);
westPoints = NULL;